The biggest challenge is to find one to purchase at a reasonable cost. 

@John BrennanYour plan sound reasonable.

The home will need some work, but I am excited about it.I would appreciate any recommendations for a reasonably priced insurance company for the unit while I am rehabbing it.

If they meet your criteria, you may not have a valid reason to decline their application.

Or you could decide that you're going to hang in there for family/legacy reasons, and keep raising the rent whenever the market supports... and whenever you turn over a set of tenants.

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. 

My dads portion of our building will be gifted to me in the will FYI.As a real estate agent, I see 5% as a reasonable market appreciation.

The only reason we don't qualify for traditional lending is because I took some time off to help my terminally ill father, and my husband has been in a commission-based role for less than a year (the lender said you need 2 years of history for that).

The reason we supply a couple packs is to avoid the cheap knockoffs. 

Screen whenever you can, there's no reason not to.