Sell one house with a pool to buy 2 without?

[Chris Gerbig]

I just purchased my 2nd SFR property in 5 months. Got great deal on both of them. Now I have to figure out what to do with my primary residence (I need to move into my latest purchase to satisfy the VA loan).

My current primary residence will sell quick for $165K.  I estimate $80K in pocket after all is said and done.   I can rent the same house for $1400 / month  minus $1100 all in expenses.  Cash flow = $300 a month.  I would have the home paid for in less than 6 years.  Problem is this house has a large in-ground pool. 

If I sell this house I will have 2 down payments and decent reserves to purchase additional investment SFR. If i dont sell it I will have a cash flowing rental (with the hassels of a pool) that will be paid for in short order. The sale also costs me +/- $10K in expenses = lost money. I can gather cash for a down-payment on a 4th property if I keep the pool home, but this will push me out of buyers market for 5 months. My goal is 4 homes as quickly as possible!

I would appreciate guidance on owning a rental with a pool in Central Florida. is it worth the hassle?

[Dave Foster]

@Adrian Smude, 1031's aren't that expensive.  Ball park a normal one of a sale less than 1 million at around $700 - $1000.  That compares very well with the 16 - 25K of tax plus depreciation recapture on a profit of 80K .

The real question is can you find good replacements that fit your parameters within the time constraints.