We've been told by a local appraiser and real estate agent that the property should now appraise for $1M+.We took a private loan from a family friend at $250,000 to purchase the property.

As long as your gross rents (per appraiser) cover your PITIA payment, then you will be good, especially with that down payment. 

Depending on the loan amount and LTV there are even some automatic issuances with no appraisal requirements. 

if you already sent him some money and he now wants more then I can tell you that you have run into a fake lender scammer.. on line profiles mean diddly squat.U can play the private lender game all you want.. just never ever send them any advance fee's unless you pay for a 3rd party appraisal directly to the appraiser..

Assuming the property is equally owned 4 ways (25% each) you could have the property appraised for confirmation of value: $1.8M/4 = $450k/share x 3 = $1.35M could be obtained as a cash out refinance, potentially utilizing a healthy portion of the STR or projected STR income to qualify. 

All of my friends worked with me (or for me) at one point or another and from appraiser, to mortgage bros to RE brokers, we had some crew in those sunny South Florida days.. 

The only way I would tell you to sell yourself in your case is if you got an appraisal.

I feel like those kind of fixes can be estimated when getting a house inspected and appraised. knowing when a new water heater was put in or when a roof was replaced, these all have life expectancies and yes accidents happen but if this is happening on a regular basis for you, like I said, I have concerns.

Apprasials allow a certain amount of lenders fees on top of the sale price and will include that in the appraisal as  acceptable to establishing value for the basis of the loan. 

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.