There's nothing wrong with considering them along with other options, but I would be careful thinking they will get you more bang for your buck or a more honest operator.Remember: cheaper doesn't mean you'll make more money.Start by going to www.narpm.org to search their directory of managers.

Contract for deed seems ideal as you could be making payments to him, which helps him pay the mortgage and extra for his apartment/travel.

Converted an empty room to a standard room to make it a 6-bedroom instead of the original bedrooms which increased the rent from $2,200 to $2,800 for Section 8 voucher holders for this zipcode.

I predict that the substantial home price cost savings and greater control they enable the buyer to have will make them grow in popularity.

Make sure to have some good cleaners, not just one, but a few. 

I'm trying to narrow down some options and do a deeper dive on maybe 2 or 3 of the best potential markets to see which one makes sense to start in. 

I had hoped to offset it with my capital loss carryover and haven't planned for any expense documentation etc. can I make the case that I am not a dealer because this is my first time and also have a high w2 income relative to the LLC profit? 

Good luck and would love to hear more about the goals you make for this year.

Make sure that your area states it directly.Otherwise, let the booking site handle things. 28 days isn't that long IMHO depending on the area or reason for traveling. 

You can make it work with an agency, but you'll need processes for auditing their progress.