So one thing I see that could be making things more difficult is the HOA requirement for same week bookings.

I would suggest asking your mortgage lender for a recommendation on insurance if you are having difficulties finding an agent that it doing what needs to be done.

Account ClosedIn my original post, I was thinking about everything I've read about long-distance BRRRR, how many hopefuls the strategy tends to find among new BP members, and the real difficulties involved in putting together a renovation in this town.

I got to 50 doors but I’m having difficulty getting to the next level.

The water and sewer bill will ALWAYS remain in the Owner’s name therefore the ultimate responsibility of the water and sewer bill will ALWAYS fall onto the Owner.See http://www.clevelandwater.com/customer-service/faq for more info.Holton-Wise does not charge the tenants for water and sewer usage because of all the legal difficulties put in place by Ohio Landlord Tenant Law and the City of Cleveland, Division of Water.

It's not without it's difficulties, but otherwise it's been a great investment.

If so, what have been your greatest difficulties (setting up bank accounts, filing income taxes, etc.)?

I'm having difficulty determining if I'm entitled to either none, all or at least 3/4 (since i live in 1/4) of the write offs when I file taxes next year.Any ideas?

I did 7.5% interest as I plan to use velocity mortgage due to difficulty proving business income. 

We have done it 4 times now.Basically your big issue will be that you may have some difficulty getting the lender to recognize the "rental income" on the house you are moving out of with regards to having the income/debt ratios to qualify on your next house.The banks typically like to see a record of being a landlord and only will recognize a certain percentage of rent (typically 75%) towards your next loan.Also we have had some minor questions come up when we moved to a smaller house or when we moved to a less expensive house than our last house.