I once had a lender who quoted me a certain rate and closing costs upfront, only to sneak in additional fees right before closing—total nightmare!

First-Time Home Buyer:Some lenders might be more conservative with first-time home buyers, asking for higher down payments or additional reserves.

I'm self employed, no other "job"I have STR insurance policies that show a line item for Loss of Business Income.

Over the past 3-4 years, most DSCR lenders have restructured the prepayment penalties to be triggered even with additional payments to principal. 

Quote from @Alan Roth: Thank you for the additional details.

Same as the experience for the self employed borrower.

I'm self employed, no other "job"I have STR insurance policies that show a line item for Loss of Business Income.

Additionally, talk to your realtor and get their feedback as well. 

This includes the seller maintaining property insurance in their name with the buyer added as additional interest and mortgage payments being made from an account in which the seller appears as bank account holder. 

Again, the seller refused (although I'm not sure if this would've been resolved legally at settlement regardless). (3) The cell tower was additionally paying a portion of real estate taxes which we were unable to confirm how much they were responsible for and if they had held up their end in recent years. (4) Cell tower had the right to purchase the lot for $1 at anytime during the lease and the right for an additional 2,500 SF of ground space.In the end we backed out at the end of the due diligence period in order to recoup our earnest money.