Thank you in advance for the help! 

The numbers vary per project, but it helps to get things done on time.

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.

I understand why carriers associate Condo/PUD construction with greater liability risk (I am sure being based in Philadelphia, a jury friendly city doesn't help either) but curious which carriers others are finding to price coverage without this exclusion and also price the coverage competitively.This also serves as a reminder to review the coverage when you hire a GC for more substantial or unique construction assignments. 

For Q1, I want to get out of analysis paralysis, pick a market and pull the trigger on my first STR. 

I will say, short term rentals require a bit more work, and if you are moving out of state, you may want to take a look into getting a property manager ( take that cost into account when running the numbers ).I hope that helps, reach out if you have any more questions. 

Help me see if this is "worth it" or not.  

Search function will help you examplehttps://www.biggerpockets.com/forums/55/topics/1227667-new-m...

Nobody is going to build "starter" homes unless there are incentives that help absorb your fixed costs - developing lots, utility connections, grading & surveying, etc.

I am hoping the Bigger Pockets community can help.