I think I will have mostly weekend or long weekend stays and am planning to go all out on luxury targeting people in driving distance for stay-cations and splurge weekends so price point will be higher than most around which I am hoping will bridge the gap in higher occupancy. 

Some may also offer a short term bridge debt option that rolls into permanent financing at a certain benchmark, saving in refi costs.DSCR lenders as I'm using it will be permanent debt financing for many investors because these loan products look heavily at the income the property produces.

But a 15.5% interest rate is at about 4-6 points higher than what I'm seeing for bridge loans.

As your seeing now with whats going on with bridge debt, some syndications are exploding (one of my 9 deals already did).

Hey @Gerald Joyce - I am a sucker for utilizing as much space in my own Chicago buildings as I can....even if the numbers don't pencil out perfectly on the cash flow because like your Ravenwood building my buildings are in Bucktown and I know the long-term appreciation will far out way the short term cash flow...The question is, with your current situation can you bridge that short coming?

I'm at a crossroads for regarding the next move strategically though with a couple bridges in sure you've crossed before.

Other than the actual neighborhood, it depends on if it is sailboat access (draw bridges or no bridges) or what the clearance on bridges is which of course determines the size boat that can be used.

If you’re not planning to hold the property, you could do a bridge/fix and flip.

East side as in the "open" or exposed ocean, or it is enough to be close to the intercoastal and bridges?  

The kew factors are: Inventory(choices), project turnover (close to close/refi), resources to make the moves, and resources to find, rehab, and then sell the flips and a lender for the bridge loans and the refis.Most people, most, will have a hard time scaling on their own, especially of their home market is un-investable to them.I keep my clients busy by opening up markets and making those key relationships and putting an infrastructure in place that will find, lend on, and rehab houses.