There are short-term rental management companies that can help with that.One that I work with in Michigan covers the entire state and can advise on local short-term rental regulations or regulations that may be on the way, they can give you an analysis of the demand for short-term rentals in that area, nightly rates in that area, monthly occupancy percentage, and projected monthly income.They also let you choose the level of service you would like from them from full service to minimal.To your success!

As @Jonathan Greene mentioned this is kind of a dated strategy in the new price/interest rate environment.

Just for fun my bookkeeper makes $50/hour which is 2.5X what the going rate for other jobs is in my area.

These neighborhoods seem to fit my goals, especially with their lower crime rates and potential for growth.Do you think these are solid options, or would you recommend other neighborhoods in the Philadelphia area based on the price range and focus on appreciation?

3) Your $250k with 30% down => about $750k (you also need funds for closing costs, taxes, etc.)

if you miss your rate lock timing and it costs you to relock who should pay for that?

My question is where do I start with funding and how would I find investors if needed?

Land is very risky, and being in hawaii makes it even more challenging - thus reason we see higher rates on land. could it be less, yes, it could be in the 15% range but i would be shocked if someone would be in the 10-13% range.

Also I've heard of some DSCR loans that are not too far off from conventional rates.  

The rates will be lower and will allow you to maximize profits.