I wouldn' be as inclined to rent.

Think of something that already has management in place so it's not on you to stabilize it from the start.If you'd really rather put the money in the stock market, but are forced to keep it in real estate, then I'd be looking at buying just one tri or quadplex in a desirable area (or commercial, if you're inclined) - those will run you over $1M and you can easily hire a property manager to handle it for you.  

But for many people (who are not technically inclined), those solutions are a big challenge to implement and maintain.  

It picks up flood and earthquake (except CA) and it even allows you to pay one month at a time (for those investors that have high turnover), if you are the property manager/contractor you can even insure a clients property for them (if so inclined). 

Wills don't change that, but they can spread the last owners interest out among everyone if they were so inclined. 

When you call you tell them that they referred you so they are more inclined to do a great job and especially if the other investor has multiple properties they will not want to lose their business either.  

When I'm "fat" (good cashflow) I'm inclined to look at acquiring High Appreciation/Low Cashflow properties.When I need cashflow I tend to look for Lower Appreciating/Positive Cashflow Real Estate.Then there's my decision to:Buy, Fix-up, Sell?

I would be inclined to buy a duplex without a VA loan and live in half while deciding where to buy my VA loan residence and finding a good deal.  

As a Broker for 20+ years, I would be inclined to work with a wholesaler in that regard for several reasons :-I wouldn't want to gain the reputation as a Broker whose Buyer(Wholesaler) does not perform-Typically when a buyer makes an offer on a MLS listing, the other Broker/Agent is going to ask for proof of funds and with the model I described above, many will provide fake internet proof of funds and again bring my integrity into question-Wholesalers using the model above are going to be marketing the property from the MLS while it is under contract which again could bring my integrity into questionFor example : While I am a Broker, I primarily flip houses and purchase many HUD homes per month. 

So if you put in an embarrassingly low Offer to start off with (because they won't let you look at it until you make an Offer) just to get a feel for their desperation or otherwise, and when that doesn't work, increase your Offer/s in increments if you are still so inclined.