This is my first go round, so it's been a learning experience already juggling contractors, some who are doing well, and some, not so well.

I average 85+% year round How much vacancy is realistic to plan for?

I’m from Oxford and my family owns Evergreens Coffee over here so I can happily do a round of coffee on me! 

This is 24 buyers.After the 6th month, your first round buyers are ready again to buy an other property from you.Now, a lot can go wrong for the buyers, and some buyers may do something wrong, stupid, and drown, die, loose their money, explode, internally combust, turn into smurfs... and can no longer continue investing.

Here are some links:https://selling-guide.fanniemae.com/Underwriting-Property-Projects/Appraisal-Requirements/Appraisal-Report-Assessment/Improvements/1069008161/What-is-included-in-the-square-footage-calculation-for-gross-living-area.htmyour Florida room if heated and cooled meets the requirements to be included in the GLA.The room must be heated and available for year-round use.The room must be finished to the same degree as the rest of the home.The room must be accepted in the market.

My friends and I could use it year round for Skiing as well as mountain biking/hiking/nature exploration.

You have to understand that Real Estate holdings are only part of a well rounded Investment Portfolio.

Those are great markets to invest in because of the year round market. 

@Michael Lutes,The short answer is this:[1] In the RM-1 district, the minimum lot area required per dwelling unit is as follows, provided that, whenever the calculation of permitted number of dwelling units results in a fraction of a dwelling unit, then the number of permitted dwelling units shall be rounded down to the nearest whole number: 325(.a) A minimum 360 sq. ft. of lot area is required per dwelling unit for the first 1,440 sq. ft. of lot area.(.b) A minimum of 480 sq. ft. of lot area is required per dwelling unit for the lot area in excess of 1,440 sq. ft.; provided that, if the green roof conditions set forth at § 14-602(7) are met, the number of units allowed is 25% greater than indicated by the foregoing lot size requirements, applied prior to the inclusion of any other applicable increases in allowable units.Click the link below for zoning use chart: (Table 14-602-1.A)https://codelibrary.amlegal.com/codes/philadelphia/latest/philadelphia_pa/0-0-0-154712#rid-0-0-0-170236You also have to check if you are located in an overlay district.

And now they received emails saying funds have dried up and they need to wait for the next round of funding.