Do you have a nice amount saved up for the activities you enjoy(I assume yes given a 30+ year in Tech plus you mentioning making lots of money already in real estate).If that is the case, what are you looking to achieve now within real estate?

Think carefully before you do this. 

Also do you use a property management company or do you manage them yourselves?

We do them, but they aren't cheap and your LTV will be lower that a HELOC on a primary residence.

That being said, I'm looking for virtual assistants to vet lists and do some other small administrative tasks and perhaps eventually start cold calling.

Also, my insurance company said it would be the same rate regardless which option I go with.or do I stick with the cheapest option upfront like a shingle roofObviously the upfront cost/future cash flow will be hurt the most by the standing seam steal roof (although it could assist in resale value)Does anyone have experience on roofing or an opinion which is most ideal for this scenario?

Jerrell,That would be a pretty simple process you could use a renovation loan or do a cash out refinance. 

Makes sense.Update - so we went to do the inspection and the power was off. 

Quote from @Joey Samudio: I am looking at doing my first remote deal.

Plus, you can do everything on your computer if you want.