If your thoughts are telling you to  wait until you're in a position that you think is strong enough financially to be comfortable with this new business, Listen to your own thoughts.

Long-term rental and a short-term rental are two completely different business/investments.You should understand what each requires and see if you are comfortable with them.Short-term rentals, on paper, generate more income but require more work.

FHA Loans are going to be essentially the same regardless of who you go with so probably just makes sense to shop for a few and pick the lender you are most comfortable with

It only tells how much you underpaid and does not tell how much impact the sale of your property made.If you want to be more comfortable with the result, pay an experienced real estate accountant to review the work of your tax guy before it is submitted to the IRS.

Any regulations, limitations, or potential that you have uncovered and would feel comfortable sharing about.

But if you are using seller financing and a regular CRE loan, the seller will need to be comfortable subordinating.

It’s important to find the right deal that you are comfortable with.

If not and you're comfortable with the current buyer, you can look into owner financing or the lease with option to purchase route. 

My comfortable price range would be between $500k-$1M.I know that under $1M, you probably won't find something new, climate-controlled, or in great condition, but is it true that there's almost nothing worth looking at in this $500k-$1M range?

Get out of your comfort zone.