Prices are high and with Hawaii STR taxes it's a lot tougher than first glance.

Creating a REI group on facebook, free to anyone who wants to join.

Im in a Vangaurd Money Market thats paying me $286 in interest risk free.

They are offered trade school or state college debt-free. 

The properties are either one street down from each other or are 2-4 buildings next door.Property #1 (Currently live in with my family and I)Purchase Date May 2021Mortgage Balance: $117,898Rate: 3.625%Mortgage payment including escrow: $870.51Purchase Price: $143,000Tax: $3,308Estimate to sell in today's market: $190,000- $210,000 based on current sales in the market this yearHOA: $110 monthly includes Water and building insurance and other maintenance for the propertyProperty #2:Purchase Date:: April 2022Mortgage Balance: $135,756Rate: 4.625%Mortgage payment including escrow: $1,375 (payment normally $1,059 but payment increased due to low balance on escrow because of tax increases)Purchase Price: $148,000Tax:  $4,578Estimate to sell in today's market: $190,000- $210,000 based on current sales in the market this yearHOA: $100 monthly includes Water and building insurance and other maintenance for the propertyRent: $1,400 a month only water is included in rentProperty #3:Purchase Date:: February 2023Mortgage Balance: $118,518Rate: 5.99%Mortgage payment including escrow: $1,315 (taxes have gone up for this property as well)Purchase Price: $132,000Tax: $4,522Estimate to sell in today's market: $190,000- $210,000 based on current sales in the market this yearHOA: $100 monthly includes Water and building insurance and other maintenance for the propertyRent: $1,400 a month only water is included in rentProperty #4: (We were thinking of selling this and take profits but not sure to be honest)Purchase Date:: February 2024Mortgage Balance: $139,408Rate: 6.75%Mortgage payment including escrow: $1,332Purchase Price: $147,000Tax: $4,130Estimate to sell in today's market: $190,000- $210,000 based on current sales in the market this yearHOA: $100 monthly includes Water and building insurance and other maintenance for the propertyRent: $1,350 a month only water is included in rent

We plan to sell and use the $500k exception to the capital gains taxes because we lived there for two years. 

It's quite freeing being able to do what you want when you want.

I'm exploring alternative financing options and would greatly appreciate insights or experiences in similar scenarios.Key Points:Property Location: Cahokia HeightsPurchase Price: $17,000Rental Income: Approximately $1,500/month via Section 8Condition of Property: Updated plumbing, roof is in good shape, needs AC unit, paint, flooring and cabinets and counter topI'm considering reaching out to private lenders but would like to gather opinions on:Feasibility of securing a mortgage for a low-cost property.Attractiveness of this deal to private lenders.Any creative financing strategies that could be applicable here.Legal and tax implications I should be aware of.Potential risks and how to mitigate them effectively.Any advice, suggestions, or contacts in the private lending space would be immensely helpful.

I would prefer to manage everything through the LLC's account for bookkeeping and tax purposes.Proposed Solution:Open a new joint personal account specifically for making mortgage payments.Transfer the monthly mortgage payment amount from the LLC's business checking account to the joint personal account.Document these transfers as "Owner's Draw" or "Owner's Distribution" in our accounting records.Use the joint personal account to make the mortgage payments.Questions:For the CPAs and accountants out there:What are the tax implications of this approach?

Or are you expecting them to invest a few hours for free?