I recommend talking with an attorney to see what options make sense for you.Once you have the ownership/legal entity situation handled, you'll know how many accounts to have.

Hey @Jeff Ryan - While I can not speak to your exact situation, I can speak to the thousands of homes I have walked here in Chicago, where majority of the homes were built in the late 1800s/early 1900s.I would say that 7/10 of the older homes I look at have some sort of settlement in the foundation, which causes the cracks and sloped floors you are mentioned you are seeing in your property. 

However, the Most alarming thing is they have allowed the water bill (they pay for all utilities, but the city bills the water to me) to mount over $2k over the last several months.

Having an open conversation about any possible contributing factors, including outdoor exposure, could help resolve the situation.

I would chalk situations like this up to the cost of doing business when the security doesn't cover the damage unless it's exorbitant.

I regularly call sellers on behalf of my buyer clients that I have preapproved and walk the seller through the rigor of my preapproval process to prevent this exact situation. 

John, not sure if you are familiar with the current STR situation in Huntsville, but the city has shut down STRs that are not zoned correctly and also not permitted. 

I also think the real estate community is rather small, so will be a situation where knowing the right people will make all the difference.

Purchase price: $665,000 Cash invested: $200 Sale price: $665,000 Its a Duplex 2bd1ba each unit, nice backyard and long driveway, situated in the Pattern neighborhood 5 minutes drive from Dimond/Laurel village.

It sounds like you’re handling this situation thoughtfully, and you're right to question the validity of the HOA’s stance.