Most look at a Certificate of Insurance and confirm coverage limits but best practices are to (1) become added as additional insured under contractors policy and (2) understand coverage exclusions which are not going to be detailed on an insurance certificate.

It can still qualify if it's a fixer-upper, as long as the rental income from the property can cover the debt service.

There is a company names Hemlane that offers that "light PM" service that may be interesting for you instead of a full blow PM company that may cost 7-10% of revenues.

In addition, the gas bills have shut off notices and are not being paid. (3 units are occupied and utilities are all paid by owner).

Feel free to private message me with any additional questions.

I intend on sending the tenant a bill for the exact repair cost as "additional rent" (per the lease) instead of evicting in the winter and deducting from the security deposit.

You CAN limit that agreement to a specific property; but, as others have stated, agents are looking for a certain amount of loyalty from their clients.If an agent gets vibes from a prospective client that indicates that they want to cheapskate and not pay a professional for their service, they are not likely to waste their time with them.

Generally, a loss can only be claimed in the tax year when the investment becomes completely worthless or when there is a final determination that no further value will be recovered.If the REIT has officially liquidated, been declared insolvent, or issued a final report confirming that no additional distributions will be made, you may be able to claim the loss on your 2024 tax return.

I've owned the house for few years and have spent a lot of time trying to design an addition to add value to the property, but the current floor plan is really not conducive to realizing a return on that investment (tiny living room, low ceiling basement, poorly placed basement stairs, etc.). 

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.