As a long-term hold investor, I see this property as -$600/mo to -$800/mo depending on whether you use a PM or not.

Depending on your state, many have local lenders that will go up to 100% LTV. 

Do you live in Wisconsin?

Typical equity build up time is 5 years, depending on your market.But can you purchase another rental using your own capital?

My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

I'm planning on buying a small multifamily first and foremost so I have a place to live and then will either buy a single family or another multi family depending on what I can find/fits my criteria at the time.

In fact, come to the USA and live off of those of us who pay taxes.  

@Ryan Cousins it's really going to depend on YOUR analysis/projections of what you think the property will be worth in the future.You'll want to compare that to any capital gains tax-savings if you sell now.

I actually live Pinellas County.  

After 45 + years as a real estate investor, broker, lender, fund manager and syndicator, I’ve become aware that the “dream” of many investors and investor “hopefuls” is to be able to generate enough cash flow to live off their real estate holdings and accumulate enough wealth to make “work” optional.