In general, this is C or C- area.

I generally purchase my tickets with cash and use points for his since I am the point / status gatherer.  

Looking for recommendations for a good General Contractor in the Norfolk, Virginia area.

Generally, if you are moving plumbing, you need a permit.

generally, the best product you can use for a cash out refinance is a DSCR loan.

I'd love to utilize their expertise when assessing a property since they are local but I'm not sure what the general expectation is when I don't have a tangible property and I have not entered into contract to work with them yet.Some questions I have are: local regulations/permitting timeline, property's potential from their perspective, landscaping/amenities cost estimate (they also help facilitate this).

As you note exiting any RE that does not have some appreciation of a significant amount over say a 5 to 10 year hold generally speaking is going to lead to a loss at sale.

I think their general stance is going to be to go with whichever comparable property has the greatest degree of similarity in terms of (probably, in this order): location, age built, quality of construction/current condition, and square footage.

In reality, most older homes will cost you considerably more in maintenance, capital expense, and vacancy (people just generally like to live in and rent newer homes).

While I can appreciate ones desire to own real estate, it is not the appropriate investment strategy for most who fall within this category & the consequences of a bad investment generally far exceed the potential upside.