DSCR loans will not be advantageous when compared to conventional loans.

Another downside is you loose on the advantages, of the Federal Tax Code, by not closing in the name of a LLC/ LLC taxed as an S Corp, or an S Corp.If you want to close in the name of a LLC/ LLC taxed as an S Corp, or an S Corp, Mortgage Lenders will offer you Commercial Loan Terms (25-30% down, a 15-25 year amortization, and a ballon due in 5-7 years).

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

If Costa Rica gives more capital gains like you suggest (which I doubt given how pricey it already is), he's going to get them with his own property and he'll ba able to take advantage of it without needing anybody's consent.I think the question is whether you can lure a lifestyle buyer into seeing it as a better opportunity than if he'd own his own property. 

I will definitely be taking advantage of trying to network with some Chicago people here.As for looking for a good tenant. 

Single-FamilyThe supposed advantage of multi-family properties is that income from occupied units can mitigate vacant units.

What is advantageous is someone that is good at underwriting and unbiased (only analyzes the deal based on the underwriting without other emotions).Note i have a fair amount of experience and plan to place a competitive offer tomorrow that the underwriting dictates not placing a competitive offer.  

For those of you that have good w2 income and want to take advantage of employer matching (100% return!)

Cincy has a pretty good section 8 program to take advantage of as an investor.

This is a great place to learn and to connect with people so take advantage of all the great resources.