It doesn't hurt to try, but it might be hard to find serious investors.1-4 family properties are looked at more like a single family residence and 5+ are looked at differently. 

Then in 3-5 years you move to your "permanent" house you will have two rental units that most likely pay for both your old home and existing.Because your cost to buy is so low < $5000 you can buy the property, shop for renovation money, maintain an apartment (small studio or 1 bedroom) while the place gets livable.If your partner does basic construction he will know people who can do the heavier stuff, he doesn't do personally.

I think the Field Foods aspect is a big plus as currently residents would have to drive to Richmond Heights, Maplewood, or Southwest Garden to get to a Schnucks or Shop'n Save.

We rent to our handyman.It's a good deal for us as we don't pay payroll taxes on the resident manager deal and for him...free rent.

We are looking to save some money on residence hall expenses over the next several years and keep the home as rental after my daughter graduates. 

However, if this is our primary residence for at least 2 years after they gift/transfer ownership to us, would we be in the clear of owing on capital gains taxes up to $250k per person (or $500k total)?

This year I am looking into moving into commercial sized multi families (5+ units) and just so happens that an interesting property went up for sale around the corner from my primary residence.

What is the tax filing requirements for FLFor 4 and 5 I suspect Ohio will need a non residency filing and the income will be taxed at the state level in Ohio.

You are right, if your house was your principal place of business, you could deduct the commuting expense going between your residence and another work location IN THE SAME TRADE OR BUSINESS. 

I could use your help with the following two questions - How do I enter depreciation on my taxes if my property was used as a rental, then my personal residence, then rented out again in the 2017 tax year?