HOAs are less of an issue for a flip or remodel prior to renting but can still cause issues if they are strict about construction hours, noise, treatment of debris, permits, exterior paint colors, etc ... even if you are respectful, follow the rules, and are in the right, an overbearing HOA can still make your life miserable.Agree with some others, BTW, the only "Good HOA" is NO HOA ... all others are varying degrees of Bad.

Prevent any person, partnership, trust, association or corporation, or the partners, officers or employees of any partnership, trustees or beneficiaries of any trust, association or corporation, from acquiring real estate for its own use, nor shall anything in this section prevent any person, partnership, trust, association or corporation, or the partners, officers or employees of any partnership, trustees or beneficiaries of any trust, association or corporation, as owner, lessor or lessee of real estate, from selling, renting, leasing, exchanging, or offering to sell, rent, lease or exchange, any real estate so owned or leased, or from performing any acts with respect to such real estate when such acts are performed in the regular course of, or as an incident to, the management, ownership or sales of such real estate and the investment therein.”

Sometimes tenants will treat a property with the same respect or lack of respect that you do.

I have a lot of respect for the conservative approaches out there.

With respect to each property's additional coverage, is that the only option for additional coverage, or is there a general policy that would cover the business, without redoing the process for each property.  

The purchase price is $107,000, while the tax value and Zestimate of the property are $165,000 and $208,010, respectively.  

So 100% of our bookings are from VRBO and AirBnB (30:70% respectively).

There are a couple REIA's here locally (you can check them out on Meetup.com or search for CIREIA and INREIA, respectively), and I believe there's a Northside meetup that's posted here regularly on BP under the Events page.

A 203k Loan is where the purchase price and rehab costs are rolled into a single loan.Assuming you have a respectable FICO you can buy, with a FHA Loan (3-5% down, a 30 year amortization schedule, and a residential loan rate).

Respectfully, Phillip