I would keep it at "reasonable market rent" (whatever that means).

Detroit is a market where local have a strong competitive advantage over non-locals so you want to use that to your advantage.

Depends on your goals and the current market.

Convention lenders said they are OK with this approach, but in PA not sure paying the transfer tax twice (once at sale and once at transfer into LLC) is worth the savings on the interest rate between the conventional vs DSCR (just pay transfer tax once at sale).

Despite rate cuts, we aren't seeing the lending market agree with their expectations on inflation.

While Treasuries are often viewed as "risk-free" investments, certain real estate deals in today’s market offer a compelling alternative—especially when purchased at a deep discount.Take, for example, a 1,000+ unit apartment complex in a suburb near Michigan.

I have been reading the online resources about getting started, searching the market, and even doing tours, but I am hesitant to jump in and buy a house as I have quite a large amount of student debt.

The two are almost entirely different markets in terms of price points, returns, tenant quality, and overall investing strategy.

Is it best to approach an architect or a land developer for what I am proposing?

If Allstate is not offering proper coverage (stress the if) and you can get proper coverage in the surplus lines market you would want to do that.