With the windows open, it helps circulate air more of course but doesn't do much of anything for the humidity levels.

Looking at least $50-$75k depending on the level of damage.

If your project is good that might work but also if your project is not as good as you thought you should learn that from the consultant once they review what you are trying to do.There are some books out there at ICSC and ULI but you would still need a consultant on the local level to give guidance.

Trust your gut. 

If you're not going to see the house yourself, you absolutely need someone you trust to do a walk through.  

If the latter, how would you approach an increase like that to someone you know on more than just a professional level?

Real Estate is a competitive game, and Internet and BP have leveled the playing field for anyone who wants to take advantage. 

But high level:1) If the units rental income doesn't cover mortgage its not going into my buy/hold portfolio , I have a separate "appreciation" portfolio for that on (think San Francisco where CAP rates are 3-4 , but if you can wait out or turn low rent controlled tenants you can improve the building profile.) 2) I am currently looking for places in B- to A- areas.

Price / Rent Ratio - lower the better Avg Median Income - feeds into #2, not as important on its ownAvg Median Price - feeds into #2, not as important on its ownAvg Median Rent - feeds into #2, not as important on its ownRent % of Income - rent should be >1/3 of incomeSociodemographic Rank - should be high (used this article)Population Growth - should outpace US average (used this site)Jobs Growth - highger the better (used Forbes data: example)Law Favorability - should be landlord-friendly (used Avail: example)State Tax Favorability - should be favorable (used this article)Poverty Level - should be low (used city-data.com)Crime - should be below US average of 290 (used city-data.com)Industries Present - should be diverse (used city-data.com) Here are the markets I evaluated: Bend, ORGreenville, SCCharlotte, NCMeridian, IDMidland, TXSpartanburg, SCHuntsville, ALKent, WAWithout any further delay, here is my market analysis laid out with selection criteria and markets: As you can see, the Top 2 Markets are: Meridian, IDCharlotte, NCand they are mostly green across the board, hitting all selection criteria, at a reasonable purchase price for my first investment at a young age.Now that I've completed a brief analysis, I'm looking to dive into deal finding and developing my Core 4.What are your thoughts on my preliminary market analysis?

You guys in CA are different kind of special, but I think you might have options with a Delaware trust - talk with @Scott Smith.4.