Real Estate is a large asset class that has many different strategies inside of it. 

There is no one size fits all answer for this question, market to market, and property to property are all different. 

Your goal of acquiring your first single-family rental by early 2025 is both ambitious and exciting.A few thoughts as you navigate this market:• Local Insight: Since regional nuances can make a big difference, tapping into local brokers and contractors who understand the Hudson Valley and Catskills can provide a valuable edge when evaluating properties.• Creative Financing: Keep an open mind to creative financing strategies; sometimes thinking outside the traditional box can reveal opportunities others might overlook.On a related note, I help investors streamline their operations by generating quality leads and assisting with VA hiring, which might be useful as you build your team and network in the area.Looking forward to seeing your progress and sharing insights along the way.

I interpretttev @Alan Asriants statement different than you but agree it is not clear   He could be indicating pools, basements, sunrooms do not provide a means for an extra tenant.  

On a larger and more complicated claim is when a public adjuster working for you makes the biggest difference.  

I would keep the deposit unless I am able to rebook the dates and then I would only make her pay the difference for any unbooked nights. 

During the "fix up" process, you would use a different kind of loan that will end up converting to a DSCR loan once you have tenants living in the unit(s).So, I would need to use maybe a construction loan for the renovations and then convert it to a DSCR loan?

Anyone else seeing success with a different strategy around the Chi?

I find it critical to test those assumptions under different scenarios when I’m looking at a deal.

You want to be understanding and not "kick them out", but at the same time let them know you operate differently than the previous owner and if they would prefer not to operate that way that's a decision they can make.