Just because properties are assesed higher doesn't necessarily mean they will go up or atleast not go up on an equal level to past. 

You can rent for anywhere from $1000/mo up to $1600/mo depending on the square footage, bedroom/bathroom, attached vs semi-detached, level of finishes and whether or not you rent to Section 8 tenants.

Given you are trying to add insulation after the roof has been redone adds a level of difficulty and if not installed properly can actually lead to other issues. 

You need (in most states) a minimum of 4 years experience at Journeyman level or higher, plus another GC to sign for and verify that experience.

. - The exemption for the top level of disability is on the assessed value of about $815k - so it is important to look at what the assessed value is, not the purchase price. 

Mid 4's should be expected with your experience level. 

Humidity levels in basement is high at 64%A/C was 40 years of age, not functionalSigns of Ice damming on the garage sheathingFurnace is 19 years of age, unit didnot fire when turned on at the thermostatThe incoming 3-wire electrical systems is considered out of dateNo GFCI outlets anywhere (including in Garage)Walkway has cracking and settlementGarage floor, concrete has typical cracking and settlementBasement floor, has signs of cracking and settlementKnob and tube wiring in the home is considered obsolete and may pose an increased fire hazard.

If you buy two similar homes on one block and flip one (to get the highest sale price) and BRRRR the other, you just did your own work giving yourself the best appraised property which will help you complete your BRRRR at the highest level.

It exposes your level of maturity as an adult.

A few questions...1) Obviously, theres a few more details that go into this scenario...BUT, at surface level, are there any foreseeable issues that I'm not thinking about?