Pivoting from institutional RE investing - brainstorming

[Alex L.]

Hi everyone — I’m looking for candid feedback from active small / mid-sized real estate investors.

Quick background:

I started my career in investment banking, and now work in real estate private equity. My day job is underwriting deals, modeling capital structures, and thinking about after-tax IRR (sell vs refi, leverage, depreciation, etc.).

Over the last few years, I’ve noticed a recurring issue among non-institutional investors:

• CPAs are reactive and compliance-focused

• Brokers push deals without real underwriting

• Big financial decisions (refi, sale, 1031, cost seg, leverage) are often made without a portfolio-level, after-tax lens

I’m exploring starting a small advisory business focused specifically on investors who own ~5–50 properties (or $3M–$50M total value).

What I’m considering offering (not tax prep):

• Portfolio-level underwriting & decision support

• Sell vs refi vs hold modeling (after-tax)

• Cost segregation & depreciation strategy coordination

• 1031 / partial sale / capital recycling analysis

• Ongoing “CFO-type” advice for serious investors

Think: helping you answer “What should I do next with my portfolio to maximize after-tax returns?” — not filing returns.

What I’m trying to learn:

1. Is this a real pain point for you today?

2. Where do you feel most underserved — tax strategy, underwriting, capital allocation, or something else?

3. Would you ever pay for this kind of advisory? If so, what would make it worth it?

4. What would make you not trust someone offering this?

I’m not selling anything here — just trying to validate whether this is actually useful before building it.

Appreciate any honest feedback (positive or negative). Thanks in advance.

[Michele Fischer]

This is interesting.

1. Is this a real pain point for you today?  No, but I do sometimes wonder what I am leaving on the table that I could be optimizing better.

2. Where do you feel most underserved — probably tax strategy

3. Would you ever pay for this kind of advisory? If so, what would make it worth it? - Yes, if it isn't too spendy and I feel like I can action the information to make favorable changes.  I could see this being useful as a starting assessment/advice, then again when events change and need another look down the road.

4. What would make you not trust someone offering this?  I would want this to be fee based, so tired of free services that are really pushing commission products.