Define, "investor-friendly" agent please.In our experience we've found that +95% of agents only have experience dealing with owner-occupied transactions - which are mostly EMOTIONAL decision based.You can ID these types of agents easily by asking them:1) If they are RE investors themselves.

And if a company needs to resort to hiring him to market their props that means those props are not very good or poor investments  There are other ways to deal with the Clayton Morris types.

We sat down and traced out a plan (i.e. paying down debt, increasing their FICO scores, saving for a down payment, type of home) and in both cases, they were ready to buy in less than a year's time. 

What property types are there in the Catskills, mostly single families, multi or other types?

This will tell you a lot about the popularity of the area.I can also help you figure out the rents of an average 2/1 unit in these area if you like.

If you decide not to do a DSCR loan, the second home loan is a popular option, but there are lots of drawbacks for investors as it is really a product made for regular home buyers.

I recognize we will not be able to offset active W2 income,  but if we do purchase an investment property that has some net positive cashflow, what are the types of tax benefits/offsets we can get? 

At a very high level a property has a “tax basis”, once you exceed that basis you are subject to taxes, whether that happens when sold and paid in full or paid over timeThe loan provided by seller financing is like any type of loan where the interest is taxed at ordinary income rates.

I'm looking for two types of people to talk to (anonymously is fine).

If you go on the "Meetup" app and type in "*my local area* real estate investors" this will be a great place to start.