Well-maintained homes: Homeowners tend to spend more time and money maintaining their homes, which contributes to the overall quality of the neighborhood.

HELOCs are usually variable rate and there may be yearly fees associated with maintaining the HELOC.

While leasing is the front door to maintaining a property’s occupancy, renewing tenants is the back door.

I've done pretty well as a relatively novice investor in the stock market, just investing in S&P 500 tracking index funds.

Its all legal and now you only have to maintain a place for 5 groups. 1) you can get a heavy cash deposit down for the ownership. 2) they pay quarterly for expenses that funds the overhead. 3) everone has a share of profit when you or they decide to sell for a higher price.

What would be the best ways to familiarize myself with construction process, while still maintaining my W-2 job? 

I understand that starting out, depending on how fast you want to build your portfolio, you could spend a lot of time at it.For those with established investment portfolios, how much time is required to maintain it?

How many weekends do you want to drive up north to find, purchase, setup and maintain an STR?

If you spend time learning how to manage well, your income will increase, you'll save time, and you'll maintain your sanity with the courage to expand.

Quote from @Chris Magistrado:The point he's making is that the agent must take responsibility for building and maintaining their business, and the Broker won't play much of a role.