I will make another post with a formal introduction in the near future but for now here is my question...I understand that it's possible to sign more than one FHA Loan if you follow the right steps. my question is this... is it possible to go from FHA - Conventional - FHA or once you stray away from am FHA style loan is it not possible to qualify for another?

He went with a builder Khan Construction, built a beautiful Mediterranean style home for closer to ~$200-250/ft.

We're also thinking about diversification into some AirBNB style vacation rentals in some nearby vacation destinations as well as some locations further away that we already like to travel to.  

There is a small town in Virginia north of Richmond (the other one) called Ashland and homes on the tracks there actually sell at a premium because of the architectural styles and the fact that the train is integral to the town's identity.

Or if the bulk of your 15 properties are in a single geographic area there's nothing to stop you from using 2 PM companies and seeing which one works best for your style over 12 months.  

Is your group a discussion/networking styled group or a membership/training group?

You have a lot of nice little suburban style homes but they're just far enough away from the larger town that they're less appealing to renters.  

Doing it, poor man's style, is not possible time-wise and accuracy wise when you have more than 1 property.

Last property I did, was purchased for 190k and comps were 240k none remodeled same style unit and sqft.

Tell your agent that you want to know how he got to the current asking price.Hopefully, he can show you at least three comparable homes that are similar in size, style, beds, baths, acres, garage, basement and condition.Then, evaluate the requested repairs to see which are reasonable and achievable.