Best market is subjective, almost all viable markets for investing have their pros and cons.

If the subject property is in an area that is highly desirable and the there are no rental comps, the data will be pulled from a distant location that may not be relevant. 

If there is debt on the property you run into the debt-financed property issue which can cause the rent to be treated as UBIT and be subject to the trust tax rate which increases to 37% extremely fast.

So if at death it is worth $5m, and of that $5m based on the waterfall agreement you and your sister would get a combined $800k - that $800k does not get stepped up, just the $4.2m that belongs to your father does.If your father is subject to estate taxes, and there are substantial discounts taken on the valuation of partnership interests in his estate - that cuts back on the step up, but it saves steeper estate tax, so it is a worthy trade most of the time.

It would be very good to hear from some executives at Baselane, Hemlane, Hospitable, who have tens of thousands of landlords across the country, share their insights into the subjects @Jamie Petraglia is asking about. 

If by real estate business you’re implying you have little or no money to invest but are contemplating using one of the guru inspired methods (subject to, “wholesaling” , fix n flip) to create cash flow, I’d encourage you to do research on the true success/failure rate of people who engage in these endeavors, the amount of money the successful operators spend monthly on marketing, and the real time commitment and knowledge and experience necessary for success.  

Limited Regulatory Oversight: Fintech companies that operate without a banking license may not be subject to the same regulatory scrutiny and consumer protection measures as traditional banks.

In fact, it’s a LOT easier to find a good / great below market deal if (1) you offer all cash, quick close, NOT subject to financing and or (2) the property is one in which obtaining financing is difficult, if not impossible.Another example of where low DP is not preferable is when we syndicate property purchases.  

This is a silly question, but if I go in, asking for information like this, how would I even approach the subject?

For example, if you find a distressed seller you might be able to take over their loan using a "Subject-To" strategy and inherit a loan at a 3% interest rate!