But for years I was just working hard without seeing any benefit and I had to keep going even though there was no light at the end of the tunnel.  

You can find these deals if you look hard, search the MLS and off market and network.

I have used owner finance and hard money mostly to build my portfolio but need some institutional refi in the future.I'm also thinking about how this affects taxes, insurance.Thanks in advance for sharing your opinions!

The one stop shopping is definitely the appeal, but remains hard to find.  

We were thinking about this now because it's hard to find good deals in our price range, so thought it might be easier to put it into a bigger deal but sounds like that's not such an option. 

The rental market is strong due to students and digital nomads.Managing a couple of tenants would not be too hard but managing a dozen, on the other hand, would be a nightmare.I am a bit torn.

Yes, they are getting higher than market rent for that specific Neighborhood, but they also have a hard time finding a S8 tenant that wants to move into and stay in that Neighborhood.

Quote from @Mani Sundaresan: If I’m financing a rehab project with a hard money loan, do I still need to issue 1099-NEC forms to my contractors—given that the funds come from a loan, which isn’t taxable income?

But don't let them know it.It amazes me how many of our members at MassRealEstate dot net have an Asset worth $300-500k Rent it for .5-1% of value and hardly pay attention to it, yet chase a tenth of a percent in CD rates;-)

Lastly I dont know about your area but out this way to get development loans you need money big time reserves and EXPERIENCE going to be very hard for someone to do this with no experience those folks have to pay cash or get partners and that is very common.