Winter doesn't bring too much extra cost as long as the home doesn't have outdated appliances and has sufficient insulation.

Since the properties are in New York you have a few extra steps you need to do to keep all of your funds out of NYs hands at closing.Here's an interesting BP thread on the South Carolina property tax issue you mentioned. https://www.biggerpockets.com/forums/725/topics/604427-south.... 

 - a study on rent cost compared to ownership cost shows that virtually every large city market it is initially cheaper to rent than own (I believe is was cheaper to went in 97 of the largest 100 markets)Miami and Florida have extra concerns:- insurance difficulties have resulted in large increase in insurance costs.  

Recently got my Real Estate License and have closed a couple deals there in helping friends buy/sell homes, helps bring in some extra cash.

They get extra sun and produce a lot more limbs and thus knots, lowering the value. 

I'm taxed in the highest bracket but even if you are not, every extra dollar you bring in puts you closer to the next tax bracket.

And if you’re ever looking for boots on the ground, I’ve got a great network of investor-savvy agents who specialize in the Austin area.I’m here if you want to talk specifics or need an extra pair of eyes on a deal you’re considering..

Not much good stuff on the market right now that can cash flow without work and on the MLS the prices don't allow for some extra reno. 

Then use the extra roommate rent income to pay down your mortgage and look to refi to a lower payment in the future (3-5 years) - so it cashflow when you move out.You could also choose the smaller unit and STR the other unit to generate more cash to pay down your mortgage and refi, so it cashflows when you move out.Bottom line: you'll have to get creative to solve your cashflow challenge!

They'll likely have follow up questions about who handles maintenance, larger SD, etc... so be prepared to quickly answer these.Value to mention:- Professionally cleaned property after each stay and exterior upkeep- Staged photos that you can share with the owner for marketing purposes- Capex coverage up to $XX,000 (might need to include in SD)- Extra $XXX per month (likely may need to pay a little extra in rent to make it worthwhile, otherwise they can collect the same amount as LTR)Also, google "Airbnb apartments" or check their website.