From what I know about Westchester County in NY, it's quite expensive.I think you need to determine whether you care more about strategy or location because it sounds like you're trying to fit a square peg in a round hole.

I also do buy and hold some on my own and in a second partnership, structured similarly.One thing that helped also is that as we started to scale up a little through the first round of refinancing, we shifted to 100% of cash input from my partner and 0% from me to adjust the balance a little.

They will request some details on the property and generate a round about idea of what the cost of the study will be and what the depreciation benefits will look like.

I plan to do another round of calling banks soon to try to secure the HELOC.

@Momar MbengueWhatever place you choose, get on a plane and go there: yes it costs money but if you are gonna invest $100k+ on a property spend the $400 on a round trip flight and spend a few ways with realtors and property managers getting to know the area you want to invest.

I know of a few STRs in the area that are rented during events but vacant the rest of the year yet Air DNA says we could have 75% occupancy year round . . . 

Here are the numbers (rounded up):- Original purchase price ~ $180K- Current value ~$230K- Remaining balance ~ $140K- Mortgage payment + HOA ~ $1,300- Current rent = $1,700To calculate ROI at the current time should I base it on the initial investment amount (downpayment) or the current equity position?

What is a good round number?

Interestingly, they've recently negotiated a re-purchase price with us IF we bring new funding to the table.The rehab is required for several reasons: (a) correct the damage the bank has allowed to happen to the property improvements these past few years (known problems include completely destroyed pool makeover; wild animals living inside the residence; flooring missing in sections of the rec center building; destruction of the decorative main entry gate mechanism; lots of dead landscaping; as well as latent defects not known to us such as working plumbing, HVAC & water services) AND (b) expansion & upgrading of the accommodations (converting the private residence to a 2-story lodge with the restaurant/bar, reception/check-in, movie room, public restrooms, gym/sauna/steam room/massage therapy room; enlarged pool & deck area with climate-controlled cover for year round use; conversion of former restaurant/bar building to a general store selling venue collectibles & wearables, selected pre-packaged foods, sundries, RV & camping items, bagged ice & a propane refill station; construction of a free-standing event center; free-standing cabins; enlarged & upgraded RV park with its own small restroom/coin-op laundry building; outdoor activity areas; new landscaping & fencing; new parking area & entry drives (personal car & RVs).We know our target audience having created and operated the former version of this resort for almost years creating an initial membership base numbering about 1,100. 

These areas have traffic year round and are close to tourist attractions.