Sometimes I have even directed troubled tenants towards assistance programs (such as single moms because there are a lot of programs for them specifically in my area especially).

Which ones will still deliver in a down market? 

Spring may be better but I was unable to sell a cheap house in October for 5% off of “market value” and only sold a $600k home in January by listing it for $580k and I still only got one offer. ($150k down, 5 year seller financing.) my point being you may get $20-$40k more in a year if you don’t need to sell. 

For your seller its an effective sales price of ask - 2% using your assumed $500,000 thats $490,000, a real good offer depending on your market.  

Analyze Rental Comps & Market Trends•Look at recent rental comps in the community—not just those from a year ago, but the most recent listings with similar size, layout, and features.

It sounds like a single family house where you will be living in the house(personal use).Therefore, you may not be getting the tax benefits you think you are.Consult an accountant.I am not sure why your sister would agree to this as well, she is losing $170,000 in this transaction and she faces the possibility of you increasing her rent.You also have to charge market rent or close to market rent or it is all deemed personal use.

By doing this we qualified for a larger mortgage because we could use the rent from the other tenant to qualify and there are better lending programs when it’s “owner occupied”.  

I’m active in the market and happy to share insights on neighborhoods, financing options, or connect you with resources.

There's no real hard and fast way or only 1 way or doing your first 2 points. your subject line suggests you're not looking to go to a large shop like a JLL or a CBRE which honestly I don't blame you those offices are usually pretty bloated.As far as monthly costs, if you are going to individually get a costar or other such license you are probably looking at $500-$1000 a month pretty easy in overhead once you have office dues, mls dues, marketing, etc. 

In the future I would like to run Facebook and instagram ads in a market that guest from.