I think that the biggest take-away for me in the project is to avoid crawl spaces - I am claustrophobic and hate to enter crawl spaces anymore. 

However, understanding their requirements—such as down payment percentages, reserve requirements, and loan-to-value ratios—is key to getting approved.One of the biggest advantages of working with portfolio lenders is their ability to fund deals that traditional banks might pass on.

I agree with @John Underwood that insurance is the biggest hurdle.

This was during the biggest run up in RE prices since FOREVER.

The main property will be my primary residence.My biggest question is, what kind of foundation would you use, (that is to code and will pass inspection/permits in Charlottesville) that is either relatively easy DIY or cheap to outsource.

In addition, if i used fixed rate financing, my biggest expense is fixed.  

If you are borrowing for renovations, you will likely have a draw fee in the $100-300 range per draw.Selling costs: biggest one is commissions.  

Rent out to roommates so I employ the "rent by the room" essentially.Pros:insane cash flowif your room offer is much better value than other places to live, tenants will stay awhilea small community can be built when your tenants become friends with eachothernever ending supply of tenants (at least in my area)Cons:CAN BE management intensiveWILL BE management intensive until you gain experience and know how to manageIf you employ this strategy, the BIGGEST risk/liability mitigator is being VERY clear from the start about your expectations and that you will evict if new tenant doesn't follow your rules.With my setup - I furnish the rooms and have all utilities covered. 

What are the biggest pitfalls I should look out for? 

One of the biggest red flags I have as a lender (who lends my own money as well as secondary market loan) is when a rookie tells me there goal is to buy 10, 20, whatever properties in the next year. my next question is how many do you own currently?