I didn’t really enjoy any part of being a landlord.

It includes HVAC filter and a few 'free' things (like one free lock out or something like that).

It all really depends on your appetite for risk.

The tenant already declined the lease break offer even with a free month thrown in.

You have used home equity lines of credit to purchase investment rentals and want to know the best way to pay down the HELOCs.Between the two properties you bought, after expenses, you have $250 a month positive cashflow to use.What I like to do is pay down some principal every month with my positive cashflow.I use my extra active income from real estate commissions helping other investors to pay down the principal even more which just frees up that credit for me to use again.I know I can refinance the HELOC debt before it changes to principal and interest as it is just interest only payments as yours are.One difference is the cashflow, I have greater positive cashflow and could make the principal and interest payment in the future with the extra cashflow I already enjoy.I always get HELOCs on my income properties as well after purchasing them to pull out as much of my downpayment as possible.

Feel free to reach out if you need any help.

Are they free & clear or have loans on them?

Feel free to reach out!

However, I don't know from a practical point of view if it's doable 2) Condo vs townhouse vs cashflow: I noticed condos  and townhouses are way cheaper in fort myers FL ( however risk of hurricanes) and maybe more opportunity for cash flow.

An LLC is not free.