Novice investor looking for a plan

[Don Pham]

Hello all! Just to give a bit of a background, I'm a pretty novice investor. I bought my home in 2010 when the 40k I was saving up for a downpayment was able to buy an entire property outright and have been house hacking it ever since. In 2016 I simultaneously lost my job and doubled down on my business, greatly increasing my income but losing my ability to get traditional financing. I understand that I could have found creative ways to finance deals otherwise, but honestly it was easier (and comfortable) to work and earn a high income while I could. In 2019, with 2 years of strong tax returns finally under my belt, it was finally time for me to build my real estate portfolio since traditional financing is now on the table. 

For context, I live in South Florida where cash flowing single-family homes are tough to come by on the open market, but small multifamily opportunities can be found albeit infrequently, and the ones that do get snagged pretty quickly. I'm trying to figure how I should be going about offering on deals, and any insight would be helpful.

I currently have about 100k in investible cash, my home is how worth about 160k, my 2016 and 2017 tax returns can support a modest 250k loan, my 2019 return will be significantly higher but I haven't filed yet at the advice of my CPA, I have ~150k in retirement accounts that I could access, and my parents would like to partner and are willing to contribute 100k. 

Strategies that I've considered are: Conventional 20% down on small multifamily properties until I run out of financing, paying "cash" (using invisible cash, HELOC, retirement funds, or a combination thereof) and re/financing, and/or getting an FHA 3.5% down on a small multifamily property, but I think the order in which I do this can be optimized as doing some will lock out others.

As I'm planning the financing strategies I'm still analyzing markets/properties, viewing, and writing offers (none have been accepted thus far), so hopefully you guys don't assume I'm being paralyzed by being over-analytical, but my intuition tells me there's an optimal order on the financing side to map out. Any thoughts would be appreciated. Cheers!