There are many folks, including myself, in this forum that can help and the more info you can provide (mainly numbers on the property), the more we can help you.

My main question is should we wait the extra time so we can hold the property longer or should we try and sell this year, take the profit and scale quicker.

I’ve mainly been looking at duplexes, but I’m definitely open to properties with ADUs, in-law suites, or finished basements if they make sense for house hacking.

I use the TX bookkeeper @Chris Seveney is referring to for my main entity, but I use WaveApps for all my other entities, and they have a free plan, and also a wizard that can help you set up your chart of accounts. 

If not, they may consider building the ADU and down-sizing into it and renting out the main house.

Mainly because Smarter Contact allows folks to send follow up SMS in 24 hours and can SMS in multiple markets. 

If you have enough money but your business is the main driver of income in most cases you can make more money putting time into the business.You could also get creative here.

And someone jumping into this as a complete newbie can expect that they have a decent chance of making some expensive newbie mistakes. 3) On the other hand, I feel one of the main advantages of passive investments (via syndication/crowdfunding) is that I can hire a manager who has years more experience than I can ever hope to obtain myself.

The main questions to yourself are: How much time do I want to dedicate to this? 

Once again, the main concern is a decreased living expense, but I also want to purchase in an area with long term appreciation potential.