@Erin Schenk I am an investor and real estate agent in Bakersfield and have considered out of state as well, but for me, I prefer Bakersfield becuase I manage my properties myself which increases my cash flow and cuts down on vacancies and repair costs. 

Then hope nature takes out the tree and insurance covers it.

In addition, the property after value add is likely to have initial cash flow and, if I am correct about the continuing rent appreciation, the cash flow will increase each year while my fixed financing is constant (a little variance due to escrow holding). 

Our published prices are for 12 months but we'll do 6 monht for +$75, 3 month for +$125 and month to month for +$250The reason for the increase is there is a lot of cost that goes into a new lease. 

It can be a hassle at times, but the increase in your ROI from self-managing is hard to beat.

How much of an operational improvement (i.e. increased revenue, decreased costs) can you reasonably expect?  

Look to ensure that its value would increase by lots more than the cost of fixing it!

I had them do this retroactively on a tenant increasing her portion $150 / month.  

An umbrella policy does not cover anything special, it only increases the amount that will be paid out in the event of a liability claim. 

Whoever you talked to at the HOA might have had an agenda or may have given you bad info so I would double check.Offering seller financing may help by increasing your pool of buyers.