Its an older home and the roof will probably need replacing within the next 3-5 yrs along with the ac unit.

Find a bank, the one you're working with or another like it, that will transition one or more of your properties onto a first lien HELOC.The HELOC will replace the mortgage; the "refinance" into the HELOC will cost a lot less, giving you more capital to invest; and you'll have instant access to cash if you want to buy more property.

That will be an extra $1500-$3000 in insurance premiums you will pay because of the claim.If your roof is $5000 to replace, and you have a $2500 deductible, you are actually could lay out more over the next few years. 

., hanging something) then just leave the plaster, do your thing, patch it and move on.If you have to disturb larger sections you run the definite risk of breaking the "keys" that hold the plaster tight to the lath, so you might find that sections start to fall down which can create a cascading/domino like effect.There are probably ways to carefully cut out sections that can reduce the chance of that happening, but like I said, the general rule is that if you're disturbing large sections you might just have to replace the whole area with drywall to be done with it.I don't have specific tips on the gas and oil changes re: RI's commitment to reduce/eliminate them.

I also plan to replace the carpet in a couple of years with LVT.

The siding is asbestos and is in decent condition but has some small replacement pieces here and there.

Siding, windows, doors, and floors all need to be replaced, in addition to a new addition being built for the kitchen that is also needed.Type of financing sought: Unknown???

The only thing I did was replace the floor with vinyl. 

We've replaced the toilet and have removed a small section of rotted subfloor with sheet vinyl flooring on top and replaced it with LVP.

I've been analyzing a bunch of properties in my area hoping to house hack or purchase as purely a rental property.