Scenario 3....you could tap into some of your equity on your current portfolio and your primary residence if you have one and start doing BRRRR's and flips to generate more capital and more buying power. 

I have the opportunity to buy some real estate property thru a buddy of mine, title in hand but she hasn't paid property taxes in the past 5 years.

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. 

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.

That can look like two buddies owning a building together or a full blown TIC sponsorship under rev proc 2002-22.