Picking up on number 2, Don, how would someone learn about an investment segment without investing before they are a master?

It's hard to stand out.There are some NEW owner-occupied segments with people who share motivating factors for selling their home.Seniors with Long-time Ownership: often ready to downsize or transition to assistance.Homeowners with Low Financial Stability Scores (FSS): Struggling financially and likely ready to cash in on their asset.Both these categories have additional advantages in that they probably don’t haven’t been updated and may have deferred maintenance.

@Joseph Franklyn McElroyI ran a quick search on Airdna and Airbnb this morning- there definitely is a market that you can tap into to raise prices on the one bedrooms to $150/night.But, if you haven't done so, I'd start with doing segmentation on your parent's guest history to understand why folks come there and determine your target market and survey them for their willingness to pay.The concept is actually very simple, and it's been done in pockets throughout Western NC. 

My goal is to excel in the rental property segment utilizing a buy and hold strategy.

@Erik Rouleau Buy and Hold is a straight forward strategy anywhere :)Which population segment are you targeting? 

One particular real estate segment that I think will probably suffer a disproportionate hit however would be the commercial retail market.

People did not have jobs all of a sudden, and with no work there was no way to get any rents at all.I understand this is an extreme situation, and is only likely in small segments of the county.  

I don't recommend getting only Absentee owners because they are getting a lot of offers to buy their property from all the other investors.There are some owner-occupied segments with people who share motivating factors for selling their home.Seniors with Long-time Ownership: often ready to downsize or transition to assistance.Homeowners with Low Financial Stability Scores (FSS): Struggling financially and likely ready to cash in on their asset.Both these categories have additional advantages in that they probably don’t haven’t been updated and may have deferred maintenance.

I would, if so I would back out the cost of capital as thought I am getting it from another person (interest and points) because of the risk in this market segment I would assume a profit of 1/2 of your proposed profit and if you would still do it for that I would do the deal from a financial point of view, but I would never personally do the deal as I am not comfortable in that market.

You just need to be sure to get a good list - which is where a list broker comes in.There are some owner-occupied segments with people who share motivating factors for selling their home.Seniors with Long-time Ownership: often ready to downsize or transition to assistance.Homeowners with Low Financial Stability Scores (FSS): Struggling financially and likely ready to cash in on their asset.Both these categories have additional advantages in that they probably don’t haven’t been updated and may have deferred maintenance.