I had started to demo the bathroom and figured out quickly it was beyond my skill level.

It's all dependent on the level of risk associated. 

We have a list of vendors that manage our problems with a phone call and a cleaning company that is excellent and almost never lets us down.I'm not sure we could provide the level of service needed to be this successful if we lived far away.  

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.