OK guys so I have 1 el cheapo house I'm doing ok with-bought it cheap its needed some repairs but it was cheap enough thats its not a big deal so here is my question:  Over the next 1-2 years I can buy a nicer house in the $100k range or 3 smaller cheaper houses- The single house will take longer to get, where the cheaper ones i can buy 1 in the next two months. . .

Too many variables not being discussed.

I hope you are charging a heavy safety deposit if you're renting out properties that small.

Most important variables are your tenant screening and keeping a close eye on your investment.  Ex's second husband was always bragging to me about how much he was renting a $20,000.00 slum house for in a bad part of Lexington, until his tenant stopped paying and caused $30,000.00 of damage.

There arent any details there to make a reply to.

Make a spreadsheet running returns on cash for both ideas. Which one puts you farther ahead in 5 years? 20?

And in many markets, you'll quickly tire of managing single houses as you scale. Harder to keep track of. I like my tenants stacked up like immigrants in a container ship so i can keep an eye on them.

I sold my single family units as quickly as i could. You couldnt give me one for free today.
I dont have the infrastructure in place to handle it.

Yearly "profit" not counting maintenance for 1 cheap vs 1 more expensive seems to be about the same, 5 years down the road I would obviously have significantly more equity in the more expensive home, but then I depend on a single tenant where the less expensive homes I break even for a year if I collect rent 1/2 the time.  I'm currently paying $890 a year for insurance that covers the dwelling and $300k liability on a house I bought for $25k- but rebuilding cost is insured between $80k-$90k. I wish I could go for a multi dwelling unit but that's years down the road

Not counting maintenance?

Unless they made slavery legal again and wasn't aware,  you need to do spreadsheets with all aspects of it included,  same as how you track your current rental.

You don't seem to be a numbers guy.  This will bite you in the ass, be careful.

I would take multi-family over SFH any day.

Like Fella said, stacked up like a slave ship.

When i bought my first 4 plex in 2012, we let them roam free at first but quickly found that if their feet weren't shackled together, we couldn't find them to collect rent.

Had one $90k rental, and one $50k rental. How much time and bandwidth can you dedicate, if time allows i'd do three $30k houses over one $90k. Depending on how  you manage, one renter could take that $100k house down to a $50k house pretty quickly, neighborhoods, who and how you rent, verbal vs. tight contract.
Sued to get $4k back to one with a decent job, took 2 1/2 years roughly at $40 a week from the courts on wage garnishment. If you have multiple empty then that multiple payments and/or yards to mow, taxes, etc. Still have the $50k rental, sold the $90k in the good market going now for $35k in equity. You name it, it will happen you have multiple house you'll have to be ruthless, you could have one with no A/C, one with a flooded basement, and one sitting empty. Plan on having a lot of liquidity, sucks having roll out $5k on a house you don't live in while someone's paying $700 a month in rent, and your cash flow basis is off.
Other guys are right if i had an ideal situation it'd be duplex's, or apartment buildings. SPREADSHEETS

I have the spreadsheets set up but Ive only been at this a little over a year, what all should I be including?  How are you estimating maintenance costs?

I'd take the chance on the cheaper homes. Buddy always said, no matter how nice the rental or how much the rent...you can always have the deadbeat tenant.

When I was looking for a home to buy around 2010, my realtor took me to a neighborhood with $250k-$300k homes. It was an REO, that was completely destroyed inside. The house was empty, but it looks like they had quite a few animals, and they defecated all over the entire house. Crap was smeared into all of the carpets, walls were destroyed, appliances and fixtures were all ripped out.

Normally, people that can afford that kind of house, don't do that.

Something I have noticed and I don't have rentals.  If a person can make it as a slum lord they will make it.  The likelihood of having to deal with crap is a guarantee with cheap properties but those skills of managing difficult people and situations are easily applied to higher priced rentals.

PM me an email address and I'll email you some spreadsheets.  

generalized rule of thumb I use is 10% of rent for maintenance, 10% for capital expenditures and 7% vacancy rate.  Then all other cost.  

if you want to get down and dirty put all things it takes to build a home in a spreadsheet with their cost and divid by their lifespan.  Then wait for a tenant that can fuck up an anvil with a feather to fuck it all up.