Since I’m approaching retirement age, my goal is to develop a portfolio that provides supplemental income and equity.I live in San Francisco, so I’ll be starting out smaller by looking into properties in my home state of Louisiana that I can rehab and hold as LTRs, or possibly STRs.My plan is to focus exclusively on BRRRR for now, doing everything by the book—specifically, the David Greene ones.

Outside reports can be reviewed as supplemental info, but we still need our screening completed to move forward.”Most serious, qualified tenants understand this.

If we sold now, we would probably lose $15-45k vs continue renting it out and pay $500/mo of our money as a supplement to make the mortgage payment (which includes high home insurance and property taxes).

Question: When you were starting out or see other recent investors do, what mattered most in enabling you to grow beyond your first property - market choice, deal structure, financing relationships, or operations?

You don't have a choice of deductible, and it might not be enough coverage for your needs, but if there's already something in place you can simply supplement it with a policy of your own and not spend too much.With regard to short-term rental liability, you can explore options like Proper (as Michael suggested) or some carriers offer this coverage as a rider (add on) to a traditional policy. 

.- Private money: I’m actively learning how private lending works and what terms typically make sense for a first-time investor.My long-term goal is to supplement and eventually reduce reliance on my W-2 income, transitioning to part-time physical therapy while building a sustainable rental portfolio.I’d appreciate insight on:- Funding structures that make sense for a first-time investor- Whether portfolio loans are realistic for out-of-state rentals- What private lenders typically look for when working with a rookie borrower- How to structure a low-risk, lender-friendly first dealI’m conservative, numbers-focused, and interested in long-term lending relationships rather than one-off deals.

Are you in a position to be able to supplement the negative cash flow for appreciation, equity paydown, tax benefits, and typically improved cash flow with hold duration?

In fact, that is literally why I decided to write the book: to set a standard for Co-Living.We do a lot of things to elevate the resident experience in our properties: community events, awesome common spaces, providing shared supplies, having a monthly cleaner, etc.This strategy is definitely a lot of management work, but it enabled me to build a portfolio that generates $10k/month in cash flow in only 2 years. 

Few are real estate DEAL MAKERS (even if they think they are).Real estate investing can grow net worth, provide cash flow, and enable the investor to accumulate a substantial “nest egg”.

I suspect a combination of stubbornness and the realization of “Oh ****, I just wasted five thousand dollars” made many of those conversations less productive.Because that work was a relatively small, supplemental part of my income, I eventually shifted to a model focused on pre-recorded, self-paced modules covering the same subjects I would ordinarily advise on directly.