I created the following chart to simplify the decision process (click to enlarge).The Bottom LineEvaluate the property based on whether it will enable you to achieve financial freedom.

You can successfully and fairly easily manage an STR out of state, however for your first one I think it can be helpful for it to be within driving distance (3 hours or less) and it will simplify filing / paying for taxes and tax preparation.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

It also simplifies estate planning by ensuring properties can be passed to heirs debt-free.

Simplified example: if all assessments would exactly double, individual property taxes would stay exactly the same.Milwaukee is currently the 2nd most competitive market for renters in the US, you can watch a video on current Milwaukee rent increases here. 

v=tBeixPk-Nhs&t=2shttps://Youtube.com/7einvestments is where I house all my videos‎Creating Wealth Simplified on Apple Podcasts(4) Creating Wealth Simplified through Note Investing | FacebookFinancing / Note Investing Books (Bold are ones I read, others are from other sources)Brueggeman, Fisher – Real Estate Finance & Investments (college textbook)Joshua Andrews Paper ProfitsFuqan Bilal Turning Distress into SuccessJim Napier Invest in Debt Alex Goldovsky Bulletproof Title Due diligenceTroy Fullerwood Power of Paper Bill Bymel Win-Win Revolution Fred Moskowitz - The Little Green Book Of Note Investing: A Practical Guide for Getting Started with Investing in MortgageEdward Griffin – The Creature From Jeckyll IslandMartin Saenz- Note Investing made Easier Websites For Informationhttps://www.NoteInvestor.comhttps://www.biggerpockets.comhttps://www.fusionotes.com‎The Note Investor Podcast on Apple Podcastshttps://fixnotes.comhttps://www.getrefm.com/ (excel training)

Quicken Simplifi feels a lot like mint.

You should seek a Lender who can provide a formal Certificate of Approval Letter upfront and help Prequalify DSCR properties in advance to simplify the process. 

@Adnan M. try Simplified Insurance in Southfield

What do y’all do to make things easier and simplified for multiple properties??