Be sure you are comfortable with the math and know exactly how much you should be getting depending on how the property performs at different levels.  

"there are plenty of reasons why a landlord should care who is looking at their property, theft and their own personal safety being the first 2 that spring to mind, followed closely by not wanting to waste their time" These are valid reasons but depend greatly on your market and who is showing the property. 

Is it dependent on how you get funding?

I think it would give it a little bump in value but it all depends on the buyer.

The tax treatment in such cases may vary depending on specific circumstances.

There are definitely options for less than $100k, just depends on how much lower - $75k is doable but less than that gets a liiiiiittle tricky (although still doable in some cases).

I invest in Boise, ID and do quite a few BRRRRs, LTRs and STRs- varying degrees of success depending on how much equity we can force and the type of back end financing we can find, but the tax benefits are great and it's a rapidly growing market and Idaho is probably the most landlord friendly state in the nation. 

Selling your stocks also has tax implications and margin is only 50% as you mentioned, that too depending on your stock profile.

I know conventional lending could become an issue depending on the condition of the property.

Depending on how hands on I am.