I bought a time share in the Berkshires (MA) back in 2014, I never use it (I prefer airbnb) and now I'm stuck paying the maintenance fees. 

I would take a look at your management agreement there may be a termination clause and possibly termination fee I would also take a look and see if there is a 30 day notice required I think probably something in writing should be sufficient but again verified by looking at your contract 

They should pretty much be there to pay their app fee and if approved (credit, income, background),  sign the lease. 

There are quite a bit of 3rd party sites and agencies that will list your property for short term for a percentage/referral fee which will be helpful as you get started. 

Some states are more tenant friendly and others the laws more favor the landlords.There are various websites for a smaller fee where you ask lawyers questions etc.

., combined pool for downpayment, rehab, professional services, etc.).On that note, I'd assumed I would use leverage and have estimated 25% down, but I'm open to interesting cash plays.I 100% insist on using property management, and all of my planning includes that cost.Ideally I'd like to hit ~8+% cash-on-cash return after all is said and done (taxes, payments, repairs, insurance, PM fees, capex, professional services, estimated cost of vacancy and turnover, etc.).

I was responding to the gentlemen that said he would like something to use in Hawaii.. you can buy weeks in Hawaii on the secondary market for as little at 1 to 2k for a week.. then annual fee is like 400 to 600.. so if you score the right ones.. could be a cheap way to have a place there to go to when you want.. 

However, if you can get $1100 SFL for $75K, I think that's still a good deal.Also, one thing i noticed that these calculators are missing are if you are using a PM (which it looks like you are), they charge a placement fee, which should def be incorporated into the numbers. 

o who gets fines, fees and the cost to move it back to two?

I'm pretty new to BP as well :)  Keep in mind that some Big White properties can have ridiculous strata fees for a two bedroom condo ($700+/mo).