You want to make sure that each step you take is correct and well founded to ensure the best resolution possible for yourself.

You should learn how to analyze property to ensure it's going to pay for itself.A couple suggestions:1.

I think it would be financial suicide to give up a 500k a year job that you know how to do and is secure to launch into thinking your going to replace it with rental income.. unless your sitting on 5 mil plus in  cash with no debt.

I’ve been securing great deals for clients in the Hampton Rd area. 

Building a trusted network of contractors will save time and ensure consistency as you scale.

Ensure the rents and expenses support the debt service and provide solid cash flow after covering the assumable loan, seller carry payments, and operating costs.Occupancy & Rent Roll: What’s the current occupancy rate?

In 2018, we had a property turn and the net cost to you out of pocket was around $500 (costs to repair minus the security deposit that was returned to you.)

You live in a $1,000,000 house and are able to secure a HELOC for $150,000. 

I would just take into account that a lower down payment will mean a higher monthly payment so be sure to run the numbers conservatively in order to ensure your STR revenue is able to carry your monthly payment with this higher mortgage cost. 

-Decreased security deposit to 1x for MTR.