I plan to sell my Vegas condo and it looks like I'll be able to make about a 35-40K return.

These are multiple assets of all sorts of things, retail, houses, condos, office. 

I avoid condos unless it is a quick flip.

The home has 6 bedrooms and comfortably sleeps 16.

The second that the ~$1400 face value of a 3 bedroom voucher is going to get you that rent rate).

I am planning on selling my Condo in Tulum, and looking to buy a fixer upper in westchester.

* How many bedrooms per units?

. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

Check "flexible" dates for a house with a pool to weed out the condos with shared pools.

House and condo.