@John Warren I don't think i have ever witnessed balanced conditions either, maybe just cyclical nature of r.e. or something else, but the trend line for appreciation just keeps up with inflation outside of the big, multi year market swings

It's the nature of the business.I wouldn't recommend hiring an agent since most agents aren't familiar or comfortable with the areas you would be investing.Your best bet is to find professionals in all facets of the process in the market you choose then fly in to town for a couple of days.

Now that I'm looking at moving and I have a solid career I am looking at what my long term options are and how to move use that first deal as a springboard for some long term success.I'm employed with a general contractor and love the construction industry so the idea of buying and flipping or BRRRR seem like natural options to consider.

If you're gonna rip out the oil, replace it with natural gas forced air(good) or ductless heat pump systems if the home is a candidate for that(much better.)

These types of debts become very personal in nature to the people on the board who are homeowners in the community, have probably spent a significant amount of money to try to get this collected, only to be in a position now of probably getting only 6 months of dues. 

If the worst were to happen and you needed money for medical reasons do you have an adequate emergency fund. 

I would like to get into rental properties specifically of the multifamily nature (quads would be ideal for me). 

I am in the process of adding additional buildings to it.My point is keep analyzing until the proper calculations are second nature.  

My brother and my wife's brother have provided quite adequately for their education. 

Just be sure adequate notice is given (look at lease, or better yet CA landlord-tenant law).