I have an HSA through my employer and I would like to do an out pocket contribution this year (2021) to make up for not hitting the max limit for last year (2020). 

I tried to rectify this with the property management company, explicitly stating that I do not agree with the monthly contribution arrangement.

They'll put around $100K while I'll be contributing around $20K.

Now here I am, ready to take it all in and hopefully contribute back to this community as much as I have received already via the podcast.Look forward to learning great things with you all, and ultimately witnessing the success of all involved here.Justin

In that case, the plan won't allow you to invest in real estate (or even rollover contributions to another retirement plan that would until you quit your job).2) If the plan allows you to take a 401k loan, that might be one option to access funds to invest in real estate (i.e. you would borrow the funds and then purchase in your own name or an entity that you own personally).Here are the general considerations regarding 401k loans.401k Participant LoansIf your 401k plan allows for 401k participant loans, the maximum loan amount is equal to 50% of the balance up to $50k.

The OA would detail all the big ticket items in the partnership (capital contributions, profit splits, liabilities, etc).

@Simon Obas Run your business exclusively as a business and you'll have much more resources to be charitable. 

I'm going to match my employer contribution at 4% but does it make sense to keep maxing out or save up for the next real estate purchase? 

I'm no expert but will provide some thoughts as I am looking to contribute to this forum more as I am about to stand up my first 3 vacation rentals, and this place has been very motivating and helpful.1) Your primary is not related to your second home, so remove it from the equation and solve that problem.First I would ask if your loan holder if you can get an appraisal to remove your PMI.

You can just search here and find a number of local mortgage brokers who contribute and know the investing game.