@Nate Hurwitz Hope my answers can help you in some way.
1) You have a clear goal of 100 units. What property class - A, B, C, D - and niche - value-add, new builds - do you want to target? Why?
In most markets/cases, the ideal investments are C properties in B areas. Kudos to you for finding a property, running the #s and understanding the value-add.
There are a few podcasts (BP and otherwise), where successful Section 8 investor discuss their strategies. From my knowledge (not practical experience), provided you do effective screening, Section 8 is not a bad deal. This is because you are “guaranteed” a certain rent every month. This makes it easier to manage cash flow.
But with every pro comes a con. In all likelihood, you will be dealing a different class of tenant. It’s neither good nor bad, it just is. After all, why should you care if the tenant is respectful, pays rent on time and takes care of the property?
With regards to the property, would you like to discuss the property details – price, rehab estimate, your proforma (don’t look at the brokers)? Would like to understand your analysis.
2) What are your investment parameters from a risk and return perspective?
This is the holy grail! @Brandon Turner has even written a book on it.
I would suggest finding a successful mentor and/or investor in the market you are looking to invest. This helps in providing perspective, understanding the ins and outs of the local market as well as investment guidance.
As someone with experience in corporate finance (dealing with complex financial issues), I can safely tell you that financial forecasting is not the hardest job. It’s an easily learnt (but tough to master) skill. In fact, 9/10 analyses are simple cash flow models that a sophomore can develop. The harder part is developing the right broker, contractor, investors and local connections. These make or break you.
3) How much capital are you willing to invest? How patient are you?
If you are an accredited investor, you can work alongside experience sponsors to learn how professionals operate. Vetting the right sponsor is another issue altogether. If not, you can attend local REI meetings. Be warned that some are actively pushing out courses/seminars/books which may not add value.
I would suggest investing a little, to educate yourself, in the short-term, in order to save a lot in the long-term.
You’re doing great by continuously analyzing deals and working different angles. Keep that up!
4) Multifamily has been on a hot run in the past few years. Attractive past returns might not be reflective of future returns. Don't believe anyone who is 100% convinced; best to have a healthy dose of skepticism. That being the case, what is your investment time horizon?
I think we all want the option to work. You’re doing the right thing by learning. But it’s hard to wait for the right investment as one can become trigger happy. Again, I would stress focusing on education and developing the right contacts. Everything else will follow.
5) Do you plan on being an active or passive investor? You can start passive and move into active. But I would find an experienced operator to partner on syndicated deals to get your feet wet. Eventually, you can invest on your own or as part of a syndicate when you establish credibility and experience.
It sounds like you’re doing great professionally. Have you thought of focusing on your companies and truly taking them to the next level? This can help you raise capital at a faster pace than through RE investing only.
For example, because I can’t just show up and compete with you, your company has a distinct advantage. Use that advantage! While you are killing it, you can invest passively to learn the business inside out.
To be honest, there is no ONE right way. Eventually, you just have to do things to understand the ins and outs. The only reason why I proposed focusing on your existing businesses is because you are killing it in them. Remember, you can make an existing business become more successful than a new one (all things being equal).
6) If you plan on being an active investor, apart from capital, what else do you bring to the table? For e.g. you have mentioned that you have a multimedia company. Are you good at marketing or designing marketing campaigns? Just an idea for you to consider how to leverage your massive talent set.
As I mentioned above, financial forecasting has become table stakes. The value-add comes with experience: what inputs go into your financial model, project-management, property management and financing.
Your solid experience in video editing and be leveraged in helping other investors in developing videos and marketing content. This is a tangible, hard skill you can bring apart from capital.