I have analyzed the hold option prior to closing to make sure that if I decided to hold, this deal would cash flow.

It's an investment and no one can guarantee what the future holds.

However, this is a difficult qualification to meet, especially if you have a full-time job outside of real estate.Don’t worry if you aren’t able to qualify for REPS status, because there is another strategy that is referred to as a “loophole”, which is the STR strategy.Per Section 1.469-1T(e)(3)(ii)(A): there are six exceptions where your rental property income is not automatically considered to be “rental activity” and thus may unlock the door for being able to offset these losses against your active income.The average customer use is seven days or less.The average customer use is 30 days or less and significant personal services were provided (for example, daily housekeeping).Extraordinary personal services are provided, regardless of the duration of customer use.The rental is incidental to a non-rental activity.The property is available during defined business hours for non-exclusive use by various customers.The property is used in an activity conducted by an S Corporation, partnership or joint venture in which the taxpayer holds an interest.If your property qualifies by meeting one of the exceptions above, the next step is to demonstrate material participation in the rental activity.

You live in NYC and are close to so many areas where you can make a more sound multifamily investment.Most of my holdings in my life have been in NY and the landlord-tenant laws never were much of an issue because of how I chose tenants, but it's certainly a consideration.

I would hold off until after the election.

Booking Management- Calendar Updates: We review booking calendars regularly to ensure everything is accurate and to avoid double bookings.Tracking Occupancy: We monitor occupancy rates and adjust prices or run promotions as needed to fill any gaps.3.

, Buy property off market to cut out some seller costs and get the deal at below-market value, Would an interest-only loan be best for your hold-term and strategy?

They also have real cashflow that lets me hold it. 

You'll probably do well whether you sell at the appreciated value, or hold on to it and get a better tenant at current market rent.

Do you know how to negotiate and hold contractors accountable for renovations you can't do?