This also helps with tax planning so clients aren't blindsided.The tools/software that clients use is as varied as the clients themselves. 

In davidson county most people book an STR to be close to downtown or at least close to somewhere cool as a secondary priority (like 5 points or 12 south for example).If you have an STR in white house it's going to need to make up for location.

The quality of available tenant varies drastically depending on the neighborhood.

Most lenders will vary how aggressive they will get based on the experience of the operator (you), but I don't know any that will lender to someone who's never done a spec build like you're contemplating.

Calculate potential returns on reinvestment in target markets.Define Your Priorities: Is your primary focus maximizing cash flow right now, or do you also value the stability and equity growth of holding onto a property in a strong market like Bend?

There are a lot of ways to crash and burn, so increasing the odds of succeeding long term should be your highest priority. you can always sell your local assets once you're comfortable managing rentals and ready for a market that better-suits your criteria. btw, kudos for being self-aware of your limitations.

But honestly, you'll want to shop around and compare a few local PMs since fees and services can vary quite a bit.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

It varies a lot and depends on the vintage of the property and your tenant base. 

While sophistication of your equity partners (private money lenders) will vary between residential and commercial, the principle of raising private capital is the same.You need to develop your own system which allows a constant stream of PML even when you don't need the funds and/or don't have an active deal under contract.For example; I raise private capital by offering free educational workshops for people with self-directed IRAs.