Of course....but you still left money on the table.Ultimately it depends on you and your comfort level....

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.