Whatever that number is, would you try to be a Donald Trump or would you just stash it and spend your time thinking about other things than money?

You can take the returns from your rental property and either stash it away for the next purchase, or use it to pay down the costs of that purchase.

Stash away some reserves.2) Buy a single family home, and rent out individual rooms to roommates.3) Rent out units and/or bedrooms on short-term rental sites like Airbnb.

No, not really unfortunately.I would suggest:- Max 401k, both you and wife- Research options for health savings or flex savings for healthcare- You have a nice photo of you with young children: open a college savings fund for children with pretax funds (research 529 savings)- Sell any losing stocks you own and take the loss to offset income- Stash more cash into the self-employment SEP retirement fund (I imagine you are selling your own company?)

And take some time to find the person that is right for you - someone who has values you respect and seems to have the right balance of work / life balance for the age they are.Ask yourself if that's where you want to be at that age.If you have family in the industry, that is a good start but its likely wise to spend some time under someone else.Walk in knowing who the person is, where they studied, who their family is, some of their interests and sell them on you.Tell them how you can and will provide value to them and their business at the cost of just asking a few question, now and again, only in the safe space of an office.Think about flipping / whole selling things other then real estate for starters such as furniture or if your handy, appliances (mini-fridges).You learn handy skills that come in useful later fixing up rentals and make money.There is a market from a cheap chest of draws , minifridge or a huge fan among students.Consider churning gift cards to build credit history..Finally, be ready to see all your planning fall to apart as life tends to do that.Have a bit of extra cash stashed away to help you get though those times.PSThink what you want of your peer but stay humble, sadly no ones likes the overachiever and RE is a people game.Your clearly doing your due diligence. 

I have a successful business I own that makes a $250k+ a year, cash stashed away, and no debt (personal).

After about a year, I had stashed up enough cash in the bank, and built a big enough business that I started to want to live on a predictable income again.

You just need to have stash of $3-5K for a rainy day in a decent house.

Vacancy - I always calculate it so at least one month of rent is stashed away over 12 months.

To bugs, and critters, drug dealers who when they moved, dismantle the stairway leading up to the bedrooms, because the stairs is where they stashed  their stuff.