It actually means I don't have to cut grass or maintain shrubs there but wondering if I should be more concerned about it since a previous prospective buyer walked away because of it.  

I help investors build and keep, sell, maintain, and offer full service for their portfolios of cash flow properties.

It costs a lot just to maintain membership ($3K/year is on the low side and $10K is not excessive ). 

About $600/mo after taxes, mortgage, insurance, and property management, but I need cash to invest further, hence the question to sell or cash out refi.With current rates and using box homeloans instant quote, I estimate that I can maintain 75%LTV, take out about ~$200K, and basically come out even after rental income.Not an easy decision right?

He agreed but only if i would also purchase a second house which was not in as great an area but was structurally much better maintained for another 70K to which I also agreed Now i didn't have the cash necessary to buy both houses but I agreed anyways thinking "If I've got the deals the money will find me".

We were able to maintain over 80% occupancy and a very competitive rate throughout the Summer.

When I bought them the Rent to home value was 1.0%+ but since the market has risen the rents are not keeping up to maintain the 1% rule. 

The only drawback is I have to maintain the loan for 2 years, if not I have to pay closing costs.

If I get raises in line with what my coworkers have gotten while maintaining the same expenses, I can expect to have the money by age 32, just 6 years away.  

I could initially maintain a month to month lease and gradually raise the rent (beginning with $300 per month) while I do the improvements to lessen the blow of higher rent.