Hey Michael,
I grew up in Morristown and lived in the city for 5 years. Here are my thoughts:
1. No one structure is "optimal". Offering preferred vs not may depend on if you're taking a management fee or not, if you're taking a deal fee or not, if you're taking an additional equity stake without cash contribution or not, if you're over collateralized or not. I did a preferred return of 8% with 50/50 split on top for my first deal, a fixed return of 8.5% with nominal upside on top for my second, and a super simple equity ownership no preference set up on my third.
2. This will vary. I bought a $102K SFR with no investors, and the regional bank I worked with considered it a commercial loan because I was doing a cash out ReFi with only 2 months seasoning on title. I could have gotten a Fannie/Freddie loan on that same house that would have been considered residential. The line between residential and commercial for many banks is not often defined by $ amount, but by circumstances.
3. Absolutely! But if you're going to stick within the federally-regulated lending market your options are going to be very few, and usually unattractive. I work with a bank in Chicago that gives me 90% of purchase and rehab costs for up to 12 months in 49 states. If I flip, 12 months is more than enough time. If I want to hold as a rental, than after 6 months I can do a cash out ReFi (commonly referred to as the Buy Rehab Rent Refinance {BRRR}) strategy and cash them out. The interest rates are much higher for those 6 months, but the accessibility to cash is worth. There's a lender in CO that does 100+% loans on purchase/rehab/soft costs, but they're only in 4 states. Point is, is that hard money is not hard to find these days to accomplish your goals. PM if you want that Chicago Bank.
4. I never invested in NYC/NJ because NJ taxes and NYC negative cash flow, but the one place that did catch my eye was Weehawken, NJ. Still cheap (at least 2 years ago) and can cash flow, basically an extension of Hoboken, protected from a massive market correction since NYC/HBK wasn't hit at all in 2008.
5. I've never worked with him on a deal, but I appreciated Richard Kilstein's level of intelligence and availability.
Also if you're looking into syndication, I'd check out @Joe Fairless Best Real Estate Investing Advice Ever Podcast. He's a master syndicator. And you won't want to miss the Best Ever Conference in Denver next month, which will dive into so many of these topics and more.
Cheers,
Ben
