I myself am a passive investor and don’t like to be bothered with property management so if I were you I would sell and roll the profits into a passive real estate deal but if you’re looking to learn about being a landlord then maybe you hold on to it.

I'm going to great lengths to roll out 95% LTV $1.5m o/o SFR, I'm also constantly analyzing fulfillment/funding times, etc, would I be doing all of that if I were the only game in town? 

I have 30 days to push back by making a payment of $3100.

My plan is to flip a few houses and roll that money back into the condo in a year or so and pay it off or down...but what's the best tax strategy for that?

Because this is residential the Rent roll and Cap rates don’t really matter to the lender and appraiser.Hope this helps.

Get a copy of the rent roll and the financial statement. 

What if you were to find a smaller number of investors that we’re willing to do it, and each time you refinance they roll their capital they just received back into the next deal?

I am on automatic email distributions, but I can't get things like broker comments, listing broker contact, attachments for rent roll or plans, etc. without sending multiple emails which is time consuming.

This is from my Craigslist ad:EXECUTIVE QUALITY FURNISHED APARTMENTS:2 BR apartment - Working Labradors - $6002 BR apartment - Resting Labradors - $6002 BR apartment - History Channel - $6002 BR apartment - Sports - $6002 BR apartment - Ocean Sailing Ships - $6002 BR apartment - Dogs Playing Poker - $6002 BR apartment - Guy Movies - $6002 BR apartment - Rock and Roll - $6002 BR apartment - Quentin Tarrantino - $6002 BR apartment - Country Living - $600AFFORDABLE FURNISHED HOUSES:3 BR house - Schwarzenegger Tribute - 2 baths - 4 beds - $10002 BR house - Garden Spot - 3 beds - $6002 BR house - Matchbox 20 - 3 beds - $6003 BR house - Forrest Gump - $6003 BR house - 5th Street Retreat - 4 beds - $8004 BR house - Grand Central Station - 5 beds - $10003 BR house - Retro - $6003 BR house - The Green House - 4 beds - $8002 BR house - 7th Street Retreat - 3 beds - $6002 BR house - 6th Street Retreat - 3 beds - $600BIG MAN CAVE HOUSES:The Hunting Lodge - 2 story - 2 baths - 5+1 beds - $1250The Taj Mahal - 2 story - 2 baths - 6+2 beds - $1600The Big House - 3 story - 4 baths - 8 beds - $1600

Vacancy is a real cashflow killer3) If after refinancing and potentially increasing rents you still don’t have adequate cashflow to fund reserves and property management (you will need this at some point in order to scale) you might consider selling the property and rolling the funds into better cashflow markets4) Investing out of state - there are many markets across the US with positive cashflow and good appreciation potential and Orlando is certainly one of those, maybe with more of a bias on appreciation than cashflow.