I am having a discussion with a supervisor to determine the maximum increase where the tenant's portion will only increase to $50 per month as that is what the tenant is comfortable with and we prefer to keep this tenant long-term.

Please let us know if anything happens with it - my first thought, of course, is if seller financing is an option since they clearly have no business operating it maybe they would be comfortable just taking a monthly payment with no additional work on their end.

He is not comfortable finding a tenant on a timely basis. 

You definitely need to be in MLS, whether you use a full service agent or a flat-fee broker depends on how comfortable you are with the process of a real estate transaction.

Not saying its for everyone, but take comfort in the fact that everyone who now owns investment properties once had no experience. 

A family with young children is unlikely to be comfortable having a stranger living in their backyard. 3.)

So let's do the following:1/ List the GP / syndication that you've had a terrible experience with2/ At a high level (and as much as you're comfortable sharing), provide a reason for why the GP / Syndication should be avoided from your experience (or an acquaintance's experience)3/ Any lesson learned to help future investorsLet's help each other avoid future mistakes and bring hold GPs/operators accountable. 

I live and invest in a classic "cash flow markets" (which has seen 8 years of steady appreciation and is hyper competitive and has very little inventory), and I would not feel comfortable to promise you quick and easy cash flow, certainly not within the time limitations of a 1031. 

I would suggest to start researching Idealista, however even before that thinking yourself where you feel comfortable to invest and what your investment plan would be.

I would put the student loan on an automatic minimum payment plus some comfortable, but not too large, additional principal payment (if available) per month, then forget about it.