I have an agent colleague in the Rochester area that deals frequently with investors.

Currently, the property is rented at $2100/month.The house, built in the 1900s, requires significant renovation, and the tenant frequently requests various repairs and maintenance, such as duct cleaning and appliance upgrades.

I had to ask questions to get explanations about frequent repairs.

Properties rented for less than 15 days a year enjoy simple tax rules, while those rented more frequently face a complex set of tax obligations.

Additionally, a higher occupancy often translates to more frequent disputes among tenants.

Their setup does not ideally support frequent transactions in and out of your account, especially if you're looking to employ the infinite banking strategy.

I also frequently ask other brokers in this space and exchange lenders so we both grow our networks.

I talk to our local Section 8 office frequently as a property manager and in the begin they made it VERY CLEAR that the minimums are to protect the landlord AND the tenant.Most likely, the tenants are not going to have excess cash flow or savings to cover any of the damage to your "upgrades". 

How frequently are office meetings held?

Gotcha, do the STR insurance policies cover hurricane and other weather events that frequent the coastal areas?