John, your diagram shows just as much free time at the end (with all the success) as there was in the beginning, which is rarely the case.My workload keeps increasing and I'm outsourcing more but I'd be a fool to think I will ever have the free time I had in my 20's.

Also, the fact you are a contractor, you will have a lot more flexibility on buying price since you probably won't have to outsource labor.

As he grows his portfolio, its great to outsource tasks like property management so he can work 'on' his business not 'in' his business. 

And when small, starting up, a smart person outsources many of these functions but as biz scales so does staffing requirements. 

Someone able to put the time in, can make some great returns in real estate as you don't have to pay the middle man.HOWEVER, you give up time, you assume all risk, you are responsible for all capital and are dependent on your experience to be successful (yes, some cases may vary as you outsource some pieces...)My point here is, it will be entirely dependent on your goals and lifestyle as what a good return is.

I am rather busy and I am willing to pay well to outsource certain items.Any suggestions on finding a realtor that would agree to something like this is appreciated.

If so, there may be additional fees for services like dynamic pricing or property management systems, especially if you plan on listing on platforms other than Airbnb.Even if you’re going to clean and manage yourself I would get in the habit of paying yourself a cleaning fee so that if you decide to outsource that you can still cash flow.I know the market can be tough at times to find the “right” deal a “good” deal but with patience you can stay in budget and achieve a higher ROI, COC and ROE.

Are you planning to do all the accounting by yourself or outsourcing it? 

Let me know if you ever decide to outsource your property management. 

So, as for your situation, I am puzzled why you want to own the MH and deal with the high lot rent when if you own only the note, you only have to worry about servicing the loan which should also be outsourced for a nominal cost.