I have high income and generate $150k in excess earnings per year which I used over the last few years to build my investment portfolio.

That gets me to my catch 22.My wife and I are hoping to get into VRBO world so we can enjoy and make more cash flow than we are currently making, but I'm wondering if we should put that off 18 months, rent out the property again and then reconvene at a better time or suck it up, lose a few thousand off the asking price and get moving on our goals...Financials - We owe 143,000 on the house (refinanced to conventional from FHA right after the seasoning period), it rents for $1850, mortgage, taxes insurance, HOA is $956, we just sunk $11,000 into carpet, paint, landscaping, replaced a vanity to get it ready to sell and I fear renting we might have to redo a couple of those things. 

Use your excess funds to buy more property. 

You'd lose your stable income and have to pay for your benefits directly.Can you merge your IT experience with real estate in some way?

However, you lose in this scenario you are the bad guy and jack the rent up.

I know might lose some rent but before offering a rent break I'd offer her a lease break.

Sorry was a fister had to say that or I lose my fist card.

Personally I would not send a letter or an email .i would drive right over there immediately walk rIght up to the door and tell the idiot to hIs face to lose the dog or he will be evicted then I’d hand him the quit or pay notice right then and tell him to improve his conduct or him and Fido will be whimperIng on the street . ..or you could kindly send him an email bake him some fresh sugar cookies and ask him if he was willing to compromise with just 3 pit bulls in the house

You do not have anything to lose they have.

I do not currently have a lot of excess cash to make downpayments on a home and am looking for alternatives to start investing more in to real estate.