Given that, I'm trying not to put all of my eggs in the basket of finding another traditional job.

The low-hanging fruit is gone, but if you're willing to work hard by getting off the beaten path and overturning a lot of rocks, you can be quite successful.My recommended two books: The Go-Giver book by Bob Burg and The Magic of Thinking Big by David Schwartz.Both of these books have to do with HEART and MIND first and foremost, and not knowledge or application. 

It seems like you have to have some serious cash to do these types of transactions if there is not such financing and/or put all your eggs in one basket and hope for the best. 

Fabric boxes and baskets are more pleasing than boring shelves.

We all get along really well and are hoping that this will become a fruitful relationship with many flips/rentals over the years.  

In terms of cash flow, the low fruit of a few years ago is long gone. 

I'm still not stoked even at my price but it cash flows nicely even in it's bad condition and there are some low-hanging-fruit upgrades I can tackle. 

Aloha,Before you request new proposals from a variety of vendors, you need to determine what, exactly, are your requirements.You should have an accurate total yard size, not "probably about"; how many linear feet of concrete edging; are there shrubs, hedges, or trees to maintain and/or trim around, and estimated sizes; other obstacles to work around or be cautious of; is loose trash, or excessive fruit dropping, an issue that needs to be addressed prior to mowing; minimum/maximum grass height expectations (address areas where scalping might be a problem, and how "rain days" are handled in terms of scheduling and charges); what type of schedule do you actually need; are you ok/is property suitable for using string trimmers for all areas, or must they use a push/ standard mower; bag and remove the waste, or blow it to specific area (that will not upset your neighbor); do you require periodic weed killer/fertilizer, and spot weed killer; is there/do you need an irrigation system to properly maintain some/all of the yard area (if so, the system should be checked periodically for proper operation and settings, and at every visit after mowing/trimming complete all heads should be checked to ensure none are broken); and most importantly, be sure your vendor has appropriate insurance to protect YOU in case of injury to your tenants, their vehicles, your property, or the workers, caused by their operation of rotating equipment or other job related efforts.

I'd like to not have most all of my eggs in one basket and maybe things will improve in the future.

She constantly reminds me to stop and enjoy the fruits of my labor, however she knows that working hard makes me happy and feeling accomplished.