However, based on our conversation, this strategy might unnecessarily complicate things.As a 1099 contractor, can I deduct all upfront expenses for the STR upgrade, as I did with my San Diego property?

Please feel free to use code VENI324 when upgrading to get your investing career going!

Making capital upgrades, such as painting, cabinetry, flooring, or countertops allow you to charge higher monthly rent because the unit looks nicer and is "newer" while also not be immediately expensed as they are depreciated items (talk to your CPA or hire a good one).

I would just focus on $800/mo. rent and tight cashflow in negotiation with the Seller and especially considering that to get that higher rent you will need to undergo and pay for some upgrades and then.... just buy it.

I would only do repairs, not upgrades for a tenant.Just make sure everything is clean and on good working order.

Please feel free to use code VENI324 when upgrading to get your investing career going!

It's a good move to keep things separate – set up a business checking account for your rental income and expenses, and maybe a savings account for unexpected stuff or future upgrades.

If you put money into the home for upgrades or rehab, you should be able to go off new appraised value.

Conduct a comprehensive cost-benefit analysis for replacing the septic system, incorporating up to eighteen months for the approval process should an upgrade to a new Alternative Treatment System (ATS) be necessary.

Please feel free to use code VENI324 when upgrading to get your investing career going!