if you're hiring a PM - let them handle it for youor, go to a REIA meeting, make friends with a realtor, and ask them to run a CMA for youor - look for other active rentals on a whole bunch of different sites and see what others are listed for

I'm not sure where to start with private money or hard money lending when it comes to covering rehab costs on a rental property that we already own.

You can track materials used to fill in your JIT processes or whatever.With a vacation rental, it is always different.

Look for properties in areas with strong rental demand and potential for appreciation.

You could always lean on a local real estate agent to handle your rental units for you if you do not want the responsibility, or if you feel you're not experienced enough at the moment. 

I had my rental property painted.

Check your local rules, but where I have rentals, the tenants need to be out by 1 pm on the last day of the month and you can organize with the new tenant what time they are moving in (eg 11 am).  

Verifying last 2 years of rental history very important!

I am wanting to invest 100% into real-estate whether it is flip and sell and/or long term rentals. 

I think another fear with going conventional is whether the house would appraise for the asking price if the orchard isn't taken into account... ir the cashflow from the two rentals.