All of this depends on your market having demand, of course. 

Please note the information provided below is a layman's definition designed to provide a basic understanding for the general audience.

Wholesaling can be a great way to learn a market and build capital, but holding rentals can provide steady cash flow and equity growth over time—especially in markets like Detroit, where entry prices are lower and rents are solid relative to costs.If you’d like to learn more about navigating Detroit, feel free to reach out—I’m happy to share some resources or insights from my experience.Best of luck in whichever direction you choose!

It simply depends on your time frame, when you want to actually begin renting the property out short term, and what the loan terms are.

@Mohit Gupta  depending on number of occupants your regular insurance can cover it, read the policy, ours covers two roomers. 

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

After that, it may depend more on the workload of the inspector.

First, most investors and owners of real estate related businesses are in one or more of the following situations1- they’re unable to duplicate their expertise that drives the ROI and they are at their personal max capacity as to time2- they’re obtaining high ROI by use of excessive leverage 3 - they’re obtaining high ROI by taking excessive risk4- they hit correct timing in the correct market, and this is not necessarily repeatable with any probabilityIn order for an investment or business to scale, we need the ROI (on a risk adjusted basis) to be sufficient to cover a PREMIUM risk adjusted return to passive investors; all expenses of managing the assets and the business, and a significant return to the “sponsor” providing compensation to him making the work, risk and time worth while. 

It depends on the type of lender, the broker is using.If a broker is using a wholesale lender, they make their money on the back end side.

I usually provide our budget as well with totals spent.