I need some help finding an investor friendly lender in the area who could help me through the process.

If we want to do cash out refinancing, custodian of the SDIRA LLc will have to make the call? 

However, a general rule of thumb is to hold it in the same taxpayer name for at least one year before making any changes.

It's worth meeting with a CPA before making any decisions. 

i think this is a decision only you can make. im in a similar boat (house hacking my primary) and considering renting the whole thing out to get a solo home for myself. certainly a lot of appeal in that, given how much work goes into the house hack. but whether or not the numbers on cash flow align is up to you. personally i dont think $150 (seems like about 12%?)

Lenders or investors who have short lock up periods but have years of experience feeding their business with new capital would give me more comfort but anyone who is just starting and is promising a rate of return or return of capital in a set period of time would be alarming because they very well could be reliant on fresh capital to make good on that promise and that usually ends poorly.

As you look to scale, just make sure to hold/build reserves for when repairs come up and take your time screening tenants as you will find a vacant unit is much less stressful than dealing with a bad tenant.

In terms of the permitting process, an architect that can self certified drawings would reduce the wait time to receive the permit. 

I have started the process you mentioned about comparing different software and that is how I landed on rentvine.  

The underwriting process is certainly more arduous than most acquisitions but through my personal experiences some of the lenders are far more knowledgeable about the requirements and make for a far easier process for both seller and buyer.