For the drafts, you can do spray foam around the windows and doors, replace weather stripping, etc easily enough. 

I'm going to list off some of the lowest hanging fruit from that perspective below:Attic/ceiling space often can be helped immensely by blowing in additional cellulose insulationWindows and all wall terminations should be examined and caulked/filled with expanding foam insulationWalls can often be supplemented with additional insulationRim joists, basement walls Look into selectively upgrading your main appliances (water heater, air conditioning, furnace) with high efficiency unitsOld fridges use a lot of electricity - you might take a look at what you have there and consider upgradingSome utilities have programs to offer rebates/incentives for upgrading much of the above so I'd look into that if I were you!

the best rate will shave some dollars off your interest and a couple dollars can really make or break DTI if the lender is using a computer to underwrite..but at 15k for a downpayment, on the homes you are talking, you will def have PMI (which sucks)...im not sure what PMI is...but 15k down on a 300k loan, leaves 285k note...you may be able to pay that note and be within the 1900/month criteria, but when you factor in property taxes, insurance, PMI, and interest, you may exceed the 1900 and won't get approved.  

We finished a high humidity basement (pipes were sweating) earlier this year with just 3" foam insulation & 1/2inch fireproof drywall (as its livable & has an egress window).

How much are you going to shave off from the normal process?

IRRRL - since this was a VA loan, depending on what rate you financed at last year you're highly likely to shave off a 1/2 percent or more if you refinance.

I had to put the foam pads on everything that touched the floor because the slightest movement would scratch the finish.

It has an acrylic window like you mentioned but has a a sponge foam border around the perimeter of the acrylic.

I'm thinking of either removing the asphalt with a chisel, filling it with foam, and then sealing it with roof sealant.Does anyone have any other ideas?

When/if your tenant(s) have minor/major disputes, is it my “job” as a landlord to get in the middle of it?