More issues arising with insurance, underwriting, appraisals, and more.

Have you gotten insurance similar to Air Cover for issues that may arise?

They will handle all aspects of renting out your second home.Long-Term Rentals (LTR): The management firm can find long-term tenants for your property, screen potential renters, handle lease agreements, and manage any issues that arise during the tenancy.Seasonal or Short-Term Rentals: If you prefer to rent out your property on a seasonal or short-term basis, the management firm can handle marketing, bookings, check-ins, check-outs, and cleaning between guests.

By offering a discount to pay electronically, you avoid any issues that arise from forcing people to pay electronically.

Our lease has a clause that makes the tenant responsible to report leaks and defects and is responsible for any consequential damages that arise from a failure or delay in reporting.

At this point, this tenant sounds like they're all bark with very little bite - I'd just keep documenting everything in writing (as it sounds like you've been doing) and sending everything to them via email as a backup as well, and only involve the lawyers if the need actually arises (e.g. if they file a rent escrow action; if you need to start eviction process for non-/partial payment; if you get them to agree to a mutual lease termination; etc).If you do end up going with the carpet replacement option, I would also recommend going one step further: in addition to replacing the carpet and the padding underneath, also take that opportunity to put down a coat or two of heavy duty Killz on the subfloor before the new carpet gets installed. 

Explain your worries about potential damage to the new porch and noise disturbance, especially if it's causing vibrations that could affect the structure or annoy neighbors.Consider Amendments: If your lease agreement doesn't currently address items like punching bags specifically, consider adding an amendment that outlines rules for using outdoor spaces to prevent future misunderstandings.Document Agreements: Whatever agreement you come to with your tenants, document it in writing to ensure clarity and as a reference in case issues arise later.If you need any further assistance or would like to discuss please feel free to DM me!

The quality of the people that you allow to live in your property directly impacts your monthly profit and also will arise when the relationship ends. 

At the end of the day, if there is a premises liability issue that arises, that management company LLC cannot stop a plaintiffs attorney from filing a claim against the deed holder.

I think that I will hold off on section 8 for now but continue to do my research in case the need arises in the future.