We are looking to scale our RE portfolio a little more over the next 1-2 years so wanted to set-up something which will help us keeping things clean and also help with off-setting business expenses.

Here’s the listing:--> https://www.zillow.com/homedetails/398-402-Boston-Post-Rd-Wa... price: $350,000My plan:Live in the smaller homeRent the larger home immediately (after light cosmetic work)Use FHA (3.5% down) + CHFA (down payment assistance)Reduce my personal housing cost as much as possibleSlowly fix my unit over timeBuild equity and eventually refinance to help fund a future businessNUMBERSPurchase Price Target:Offer target: $260,000Expected seller counter: $275,000–$300,000Currently listed at: $350,000FINANCING (FHA + CHFA)FHA 3.5% downDown payment covered by CHFA assistance programEstimated interest rate: ~6.5–7%MONTHLY PAYMENT ESTIMATES (P&I + Taxes + Insurance)At $275,000 purchase:Mortgage (P&I): ~$1,775Taxes: ~$420Insurance: ~$150--> Estimated Total: ~$2,350/monthAt $300,000 purchase:Mortgage (P&I): ~$1,940Taxes: ~$420Insurance: ~$150--> Estimated Total: ~$2,510/monthRENTAL INCOME ESTIMATE (Big House)Based on local comps:Low: $1,700/monthTypical: $1,800–$1,950/monthStrong (clean/paint/update): $2,000–$2,100/monthMY OUT-OF-POCKET HOUSING COST AFTER RENTIf I rent the big house at $1,900/month:At $275k: ~$450/monthAt $300k: ~$610/monthIf I rent at $2,000/month:At $275k: ~$350/monthAt $300k: ~$510/month(I currently pay $0 in rent living with family, so my goal is to keep my costs low while building equity.)REHAB ESTIMATESBig House (rent-ready):Cleaning + paint + small fixes: $1,000–$3,500Optional cosmetic upgrades: $2,000–$5,000Small House (my unit):Cosmetic repairs only: $500–$3,000Optional improvements (done slowly): $2,000–$7,000Major systems (worst-case ranges):Roof: $8k–$12kBoiler: $4k–$8kElectrical panel: $1,500–$4,000Plumbing repairs: $500–$2,000 typical(Inspection will tell me more.)CASH NEEDED TO CLOSEWith CHFA:Down payment: $0 out of pocketClosing costs: varies, but often reducedExpected out-of-pocket: $1,400–$1,800Inspection: $400–$600Appraisal: $500–$700MY FINANCIAL POSITION(To give you context for risk tolerance)Income: $5,000–$6,000/monthMonthly bills: ~$2,600Emergency fund: $10,000Credit: 717Access to 0% APR business credit card (likely $8k–$12k limit)Currently pay $0 rent (living with family)MY QUESTIONS FOR THE COMMUNITY1.)

You can book it as:Intercompany receivable (LLC #2)Intercompany payable (LLC #1)That keeps things clean and traceable between both sets of books.4.

A clean, realistic scope of work and conservative ARV will go a long way in getting a lender comfortable.The other big lesson is that certainty beats chasing the lowest rate.

So, I do agree with hedging your bets and serving a notice to pay or quit.The issue with them not paying rent and you using the security deposit is that they have zero incentive to clean the unit and if they damage it, you have no additional funds.If it were me, I'd serve them an eviction notice and then mark them as owing on a credit reporting site(I use Front Lobby).

Adding time to a task makes it exponentially difficult and if you or anyone gets in over the head you will lose the property, lose your borrowing power, and lose your money. 

A clean way to handle this is to be transparent with the tenant early and give them options.

I would do exterior landscaping, clean up the outside if that applies.

Margins are thinner now than they were a few years ago, especially with insurance and cleaning costs up, but a strong product still wins.On the Florida coast, you get more variety — think smaller beach towns like New Smyrna, Cape Coral, or Anna Maria Island — less saturation but also more local regulation.

moving the fridge and oven for cleaning - uncommonscreens, holes, rotting porch, messy porch - PM should handle these and bill youBased on your ability to get stuff done, your standards, and their service level, self-management seems like the right answer.