She was also an educator serving our community and now we are both Realtors in MA/CT.We are seeing on-market and off-market Multifamily and commercial opportunities popping up frequently. 

If there was no appreciation, there is no need to do a 1031 exchange.I have never been a fan of condo's as you lose some control over the investment - You have no control over the monthly maintenance fees, you may not have control over who is on the board, you have no control over special assessments.I wish the investments turn out well for you!

This isn't always the case, but in general, I've found Section 8 homes tend to require more frequent minor repairs.

There are circumstances that having a low downpayment is beneficial, but personally, I'm not a fan of PMI if you can afford the 20%.

As a college student landlord you may have interaction with parents & if they find you unprofessional that may raise red flags, but if you have your s**t together you can ease those concerns.I am a big fan of college rentals.

Tax-wise, profits are taxed at your ordinary income rate, and frequent flips may subject you to self-employment tax if classified as a dealer by the IRS.

Tenant can't really use this against you - if you do everything better going forward.Go to local landlord-tenant court and write down the attorneys that appear most frequently. 

I'm a big fan of value-add opportunities, whether it's buying something currently undervalued & fixing it up to my standards, or buying something that has additional income opportunities that have yet to be incorporated. 

How are you managing your properties in that area given that property management company seem to be extremely unreliable and seem to go under quite frequently 

@Dave Tasset I haven't personally invested with this company but have heard good things about then. 7e Investments, Chris posts frequently on BP.