Sell and reinvest before major CapEx? What about transaction fees

[Jack B.]

 Is it best to sell some of my houses next year and reinvest via 1031 exchange into a more expensive property in an effort to avoid capex and as a side benefit, increase appreciation potential? Or perhaps reinvest in a cash flow rather than equity market so I don't have to worry about the market tanking? During an up market, the appreciation gains will be better here on a more expensive property, and although I don't expect the market to turn for a few years to come, it is a risk once I buy, as the market could turn, whereas right now even if it turned I could sell and still reap huge profits. But if I hold I'll have to pay out capex. I could as I said, mitigate the risk or market turns by buying cash flow properties in say, Florida, where I plan on moving in 5 years anyways. So I can either buy here for more appreciation or there NOW for cash flow, instead of waiting the 5 years and slowly accelerate my plan relocation.

Although I was planning on selling in 5 years and moving to Florida, I'm coming up on major cap ex for two roofs, paint, furnace, etc. I'm not even sure I can avoid some of the capex to sell, as the roofs may need to be replaced to get financing. I'll post pictures of one of them below. The other one is in much better condition so if this one passes muster the other one will likely too.

I've had the properties 4-6 years and I've heard it said that it's best to sell within 3-7 years to avoid the capex and reinvest the money from one house into two, etc. Of course when I sell and repurchase I'm hitting transaction costs, which I will hit twice since I planned on selling all of these houses in a few years and reinvesting elsewhere. But if I need to avoid capex, I'll get hit with transaction costs twice, once now and once again later, which will basically be more than the capex probably.

Front of house worth about 270K

Back has a section with some moss I could remove....

Another back section with less moss