As I've been looking for a while close to home, I'm considering expanding my search to anywhere around a 5-6 hour drive away (my parents and younger siblings still live in SD, and my work which I can do remote/flex is based in San Diego).I'm considering new markets and interested in feedback on what areas anyone suggest I start to narrow in on. 

For investment properties, you can get a private money DSCR loan or hard money loans that are asset-based. 

Based on comps from sales in the current market.2) How much will it cost to get the unit saleable?

All new LPs should at least run some of the ugly scenario numbers, based on the legalese in the OA/PPM etc. and see if the docs are really as risk aligned as they should be and/or are claimed to be.Most PPMs list a fee as a percentage and not with the dollar amount.

The other two units that you yourself are not occupying have to cover mortgage payment based off of rent schedule.

This isn't even close to a comprehensive list, but the point is that you need to learn the pitfalls of each building based on the year it was built and do the due diligence so you don't buy a lemon. 

-Real Estate is a Contact Sport...you can have a successful real estate career based on the number of people you know and keeping in touch with them on a regular basis throughout the year. 2) Can you "keep your day job" while you get started?

Someone might google things to look out for when buying a property, see 1960 and think "well I am looking at a 1975 house", so this does not apply, when in reality, many (but not all) still apply to every property.As for testing, Cincinnati requires a pamphlet to be provided to tenants, if the house may have lead based paint.  

They reached out to me weekly for the first couple of years with issues based on their incompetence (I was happy to help, to a point, but it got old), and the purchasing company lost close to all the doors in the first 5 years due to poor service, poor systems, and not really understanding how to add value to the client.  

My 10-year goal is to own and operate 2-4 short-term rentals in lake-based vacation destinations and provide add-on hospitality services to further my mission and cash flow.