The nice thing about doing long drives as a semi-truck driver is that it allows you ample time to listen to BP podcasts and other related material to really boost your knowledge and mindset.

Gary,You have a very tough and sepcific loan requirement. 

Factor in that with rising wages, rising material costs, and general inflation.

It's all up to what you're looking to do and if you can "afford" to break even for a while and wait for appreciation but there's no guarantees with that and could leave you in a tough spot.

It's tough to give much of an opinion without actual numbers (the value of the house you have now, the loan balance & rate, your current piti (principal, interest, taxes, & insurance + mortgage insurance where applicable), rent from upstairs tenant (you're declaring on your tax return so you can use it for your next loan application, right?).  

Plus, it's really tough to cashflow in this market, unless you can find a small multi-fam with value add opportunity (I've got one at $900K). 

For general information though, I think the Best Ever Apartment Syndication book by Joe Fairless is tough to beat for an all encompassing apt syndication book.

@Anthony Thompson most of my deals/network is in Boston however RI is looking promising in a few sectors primarily STRs in Middletown, College/summer rental combos in Ganset (regulations are tough though) and rehabs/LTRs in parts of Providence

My opinion is that for the Lakes Region, STR is a tough equation in terms of ROI in our limited experience.

But at the prices you are paying now I think it would be tough to ask for big appreciation gains.