Having read all your replies, I think  going a four place would be better, but I found this and want to know your opinions, and of course if there's another one off the same list I should consider, then please do mention it.
https://www.trade-a-plane.com/search?category_level1=Single+Engine+Piston&make=CESSNA&model=150H&listing_id=2266098&s-type=aircraft
OR
https://www.trade-a-plane.com/search?category_level1=&make=CESSNA&model=150H&listing_id=2182576&s-type=aircraft&s-seq=1&s-lvl=4
There's 1,014hrs TT and 457hrs SMOH and $2,900. between the two

Pro:  it's simple, economical, looks good, and has low hours.

This one might be even better, but most of what I've flown were cantilever wing, but that's not a game changer.
https://www.trade-a-plane.com/search?category_level1=Single+Engine+Piston&make=PIPER&model=CHEROKEE+140&listing_id=2265945&s-type=aircraft

Please do keep in mind that for all intensive purposes I am a beginner.
Best life lesson I ever learned was that "I'm no where near as smart as I thought I was."  

I'm still waiting for the owner of the Cherokee to respond to my question about the hail damage.

Would I be wrong in assuming that hail damage would really be cosmetic and not effecting it airworthiness?  (outside of broken glass, or other damage)

Since I've been considering this aircraft as well I did some research and the consensus was that hail damage, unless extreme, is not going to impact flight performance.  It may cause problems with the paint depending on how bad it is.  However it will suppress the value as you can see.

I noticed that one of the 150s is described as "newer paint", while the other one is described as a 10 on the outside with "new paint".

My experience (never bought a plane, but I've worked on way too many that the owner had recently bought it with "new paint") is that "new paint" in the description of a plane for sale is a warning to be very cautious.  

If you don't know enough to be able to inspect the plane yourself, find someone that is qualified to inspect it, that you can trust, and listen when they start pointing out problems.  Don't let the paint job sell you the plane.

I haven't been in a 150/152 in about 25 years but if memory severs me you can only put about 340lbs into with full fuel.  How much do you and whoever else putting in it weigh?  Plus your stuff?

ouch, I thought it had a higher weight rating than that...average man goes 180 and I'm way above that at 265.  

When it was designed, the FAA considered the average man to be 170.

Last time I logged time in a 150, I was 180-200 (six foot), and my instructor was skinny as a rail.  During cold weather, with coats on, we could just barely get the doors closed (no wiggle room, once the doors were closed).  

Last time I worked on a 150/152, I was 230-240, and if I tried to cram myself in there with somebody else, I would have to get in first, get settled, then let them get in (no coats).  If they had gotten in first, somebody could have easily gotten injured while I was trying to get in.  Not a plane known for elbow room or being able to haul weight.

HUGE difference between the 150/152 and the 172.

The 140 you linked with the new engine or 50hr engine. Has 20 some year old baffle seals on it, completely useless in the condition they are in. TCM requires new baffle seals at overhaul per SB97-6B.  I'm not sure on the lycoming engines for required parts at overhaul but in my opinion that shows poor maintenance even if it's not required.

Whatever you decide you like have your mechanic (an independent party, not the guy who has been maintaining it) do a pre purchase inspection before you even think about negotiating price.

Have you been inside a 150/152?  I did most of my PPL in one.  I'm 6'0''/175, my instructor was a little shorter and maybe 190.   We were crammed shoulder to shoulder like sardines.  Just enough room to lift an arm to change radio frequencies.  It was awful.  

I wouldn't go any smaller than a 172.  Check out Piper Cherokees with 180 engines.  They are "cheap" and provide good bang for the buck.

Overhauled engine with the old baffle seals put back on, leads to the question of engine accessories and whether or not the old ones were just put back on the engine without having them overhauled.

Saw that recently at work.  Previous AD research just casually wrote some accessory ADs off as not applying due to the accessories having been overhauled when the engine was overhauled.  But reading the entry for when the engine was reinstalled after overhaul, they put the old accessories back on, without overhauling them.  There were several airframe ADs that were signed off year after year as having been complied with, but a visual inspection showed that they had never been complied with.  Sloppy work tends to snowball (and get expensive to straighten out).

Sounds about the same: Last time I flew a 150 I was about 220 (I'm a long legged bastard too) now I'm 260 dressed in a coat and work boots, so perhaps the 150 isn't a good "fit"     Too bad because it's close to my AO.

On the baffle seals: do they require A&P replacement?  FWIW: I'm a Heavy Truck/Special Purpose equipment mechanic with experience working on non-airworthy Continental and Lycoming engines. (Airboats)

OP,,Stop messing around and buy a 182. It will haul you and just about whatever you can fit in it with ease and comfort. Flies just like a 150/152/172 does. It, with proper care, will last you for a LONG flying career. Sure it has an adjustable prop. Big deal. You need to learn about engine management anyway. I have over 3000 hours and learned in a 150 and then jumped to the 182. I should have STARTED in a 182. We went on to a 210 and then finally to a six seat straight tail Bonanza. If I were to ever start flying again I`d go back to a 182 for a lot of reasons. Cheaper annuals, lower insurance rates, no retractable gear issues and on and on.

The FAR's line out what a licenced pilot with out a&p can do,  it's mostly preventative maintenance like tires, oil changes and spark plugs. I can't remember the list or chapter it's in off hand. I'd avoid that thing my self because the simple fact is the baffling had to come off for the overhaul and to not strip off the seals and replace them before reinstalling everything is lazy ass and complacency. The baffle seals material are cheap, enough to do it right is less than a new set of spark plugs unless they just reinstalled them too. The owner prolly doesnt even know that the shit is shit because the installing agency didn't notify him, or maybe they did and he didnt want it but maint didn't put their foot down, idk. What else is his maintenance guy or the owner for that mater lazy and complacent about?
I've had plenty of new customers awfully mad that their annuals were being just signed off with  oil changes and filters for so many years by someone else and then also a few that took the unairworthy entry and ferry flight it back to their regular mechanic because they thought there was no way their plane was in that condition.

Been ages since I looked at the list of preventative maintenance that owners are allowed to do themselves (oil change, filters, sparkplugs, etc), but I think replacing the baffle seals would not be on that list.

If not installed properly, it could cause overheating issues (which is why they are supposed to be replaced when the engine is overhauled/replaced).

At least they were accounting for accessory Ad's. I had a new customer annual a few years ago with no accessory compliance data. Found the transponder hadn't been marked for AD compliance, among many other discrepancies,  he was appalled and took the unairworthy entry because it had been through "3 annuals" since he got it and his other maintenance shop ferry flew it out of my place. Scary shit the retards do out there.

Yep.  Happens more often than it should.

At Colemill, we used to laugh at how old the pneumatic system filters would be on Barons and Navajos that came in for engine changes or conversions.  10 years was pretty common.  Wasn't too rare to find foam filters (the pneumatic pump inlet filter on the Navajo) that had just rotted away.


"But the other shop is so much less expensive..."

How hard can an annual be?  They make a rubber stamp to do it with.  Just smack the stamp down on the ink pad, smack the stamp down on the logbook page, then fill in the blanks and sign it.  "There.  Inspected."  Simple as that.

You're probably right, and returns to my original post of "Go as large as you can or stay small" A 182 is at this time out of my budget...in another year or two yes, but that essentially scuttles the idea of owning instead of renting.

Now for the Devils advocate side: "If it fly's, floats, or fucks; RENT IT!"

BTW: There used to be a 185 Sky Wagon on floats near me; I could stare at it for hours.  

It's very tempting to "price shop" for a first airplane, just keep in mind that you will most likely flip it after a year. Those basic, cheap airplanes have very limited usefulness except for "flight training" and you will quickly grow tired of the lack of power, speed, range, and lack of payload and comfort. Upside will be that they're easy to sell IF kept in nice shape. Do yourself a favor, spend a little more and get a 172, Cherokee 180, Grumman Tiger, etc that will be way more useful.

A 172 isn't a 182, but it can do a lot more than a 150 or 152 and is upgradeable (if you want to spend the money on mods, instead of trading up to a bigger plane).

I built a lot of time in a 152 and I'm no small guy.  They are what you make of it.  I can tell you my legs were no longer that 2 hours though 

Same here (only I was about 150 pounds).  People harp on range, but I always found it was either my, or a passengers, bladder that affected range more than the fuel tank of most airplanes.

On long trips I can go three hours, then two from there on out... I asked my Doctor about the sharp pain in my knee and he said it was "movie theater disease"  Turns out it fairly common for folks to get a pain above their knee caps from sitting a couple hours with their legs bent a little and a Movie generally lasts two hours.