Let’s share some insights and maybe even explore opportunities to help each other out.Looking forward to the discussion and learning from the collective wisdom of this community!

I'm very interested in creative financing options with sellers as well.Right now I'm using propstream to help assist in data collecting to focus on off-market deals. 

I'd be happy to make a unbiased recommnedation if helpful.

What loan product can I use to keep my current property , rent it so it can help pay for the loan while I build the second property ?

The neat thing about buying the STR subsequently, is that you can use estimated short-term rental income to help qualify for the STR purchase, but only if you purchase the STR after your primary (not the other way around - see Scenario 1 above). 

Howdy BiggerPockets Fam, I feel like I'm in a good place  to finally pull the trigger and invest in my first multi-family property.

There is no right answer, but I can tell you that having a full time employee to help with maintenance has made my life so much better! 

Yes, we can help out here. 

However, if you are going to take advantage of cost segregation, I would recommend working with a CPA that specializes in real estate such as Michael, Ashish, etc. or I'd be happy to provide additional recommendations rather than doing it yourself through turbo tax.Here's an article with additional FAQs on cost segregation studies that you may find helpful.

(biggerpockets.com)When assets are damaged: How a cost seg study helps if an asset gets damaged!