I rather have multiple people submitting bids on my deal rather than one person (Which is Possible if CAP Rates are high in the subject market).

I know it’s subjective, but how risky is too risky with this?

I also have a business partner who's in a similar situation to me with learning and ambition, and he and I have been outlining our goals, strategies, ideas, etc., so I won't be going at it alone and do not have to risk everything of mine necessarily.

Subject-to.

After getting rejected on the duplex house hacking idea 2 years ago, I’ve now been listening to the BP Podcasts out loud while cooking dinner to let her know I’m interested in it so she wasn’t totally surprised when I broached the subject last week and asked when she thought we should get into it.

I even mark paragraphs that pertain to specific subjects, like repairs and inspections, disclosures, HOAs, and contingency removals.Flavia Brown, Los Angeles County. homesbyflavia.com

Hello, hope you are healthy and safe.I'm very aware of section (s.) 212.02(12), Florida Statutes (F.S.) which states ALL money collected from a tenant in a Commercial Property is considered rent and as such it's subjected to Sales Tax (5.5% + 1% Miami-Dade).I have a BIG objection with this statue.

@Jonathan SantiagoThe tax difference between capital gain vs ordinary income is HUGE.Capital gain - Preferential tax rates if long term at federal level, subject to regular tax at state levelOrdinary income - taxed at marginal tax rates at federal level + Self employment taxes + state taxesIntent is what differentiates between a real estate sold being subject to capital gain treatment vs ordinary income.

@Benjamin Papet, as Mark mentioned, you typically only have 1 mortgage on the property at a time, so as he outlined, you will have invested $50k in cash, but then refi and pull out $32.5k to use how you with.In your example, you will want to look for properties that say cost $100k and take $30k to get to about $175k-185k in value. 75% of $180k, for example, is a mortgage of $135k, of which $80k pays off acquisition mortgage and you have $55k left over to find another deal like your first, and you can repeat in definitely.There are another few factors to consider: debt service coverage: the ratio of your net income to mortgage payments. 

Blanket statements about S8 being all good/bad is oversimplifying the issue: it’s simply another means of tenants’ paying their rent and should be considered independent of the formal, written rental qualification standards every landlord/PM should have outlined well before they start showing rental units.