The shingles are likely laid on wooden slats.

@Paul Caryl , Based on court cases removing and replacing all of the roof-covering material were deductible repairs because the purpose of the work was to prevent leaks and to keep the roof in good condition.However,  when the roofing material was removed down to the building's wooden structure, a new roof-drain added and a new roof reapplied (with the replacement roof expected to last 20 years), the court found that the existing roof had been replaced, so costs were capitalized. 

You just start racking up 'Days On Market'. plus I'd say you could ask a higher listing price if you wait just a bit.Just my $0.02

We are pumping in some sweat equity: killing all the weeds and doing a non-organic mulch and river rock yard, power wash and paint the wooden fences, resurfacing all cabinets, faux-marble epoxy on the counter tops, and redoing the floors (there is a mix of scuffed up hardwood and wood appearing panel...looking to just make it all panel).

Living in a small community is nerve racking and seems to be increasingly difficult as the tenant pool isn't as vast as a larger city.  

The first consideration, in my case, was that I could afford the first loan since the property I took the loan on for the downpayment was rented and would still cashflow even after I took that loan.The other consideration I made was ensuring that the new property I was acquiring would also at least break even with the monthly payment for its loan.The third consideration was that I had enough money saved not for the downpayment but for at least five months of payments on both properties in case I couldn't pay the loan in case of an emergency (you never know if the new property will rent immediately or when you will have unexpected costs associated with either property, etc.)All three considerations were very important to me, but for my peace of mind, number three was the deciding factor.With this strategy, it could seem that I am making less money since I am racking up new debt on the rental I owned to begin with, but the way I see it, the appreciation I will get in a few years and the actual cashflow that I am still getting were completely worth it.

The attorney I'd been working with is MIA (great sign I know.. will be looking for someone new), but I don't want to delay sending them a letter.Do the more seasoned folks out there think I should just rack up $200 in standard supplies and send the note to them?

I just had to replace a bedroom door after a vacancy & found the right one buried in the barn already painted ready to go.I just rented another unit at a much higher rate that has several older nasty wooden windows & now regret not replacing them during the rehab we did 2 years ago.

He said the key is having both the personal line of credit and refinance coordinated with the lender so that they know what’s going on; otherwise racking up the personal line of credit could potentially negatively affect your debt to income ratio (DTI) and cause problems when you go to refinance it.

Like you I grew up in upstate NY (up on Lake Erie) and I remember back in the early 1980s swapping out old wooden screens and storm windows from the out on my parents circa 1900 victorian home.